18442-22-3|7-Bromochroman-4-one| Ambeed

Structure of 18442-22-3

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Quality Control of [ 18442-22-3 ] Purity: 97% SDS Specification

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Product Details of [ 18442-22-3 ]

CAS No. :	18442-22-3
Formula :	C₉H₇BrO₂
M.W :	227.06
SMILES Code :	O=C1CCOC2=C1C=CC(Br)=C2
MDL No. :	MFCD09744055
InChI Key :	DMEAYYYHWLCPCD-UHFFFAOYSA-N
Pubchem ID :	22335736

Safety of [ 18442-22-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 18442-22-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	48.71
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.13
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.07
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.41
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.76
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.08
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.29

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.92
Solubility	0.272 mg/ml ; 0.0012 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.25
Solubility	1.27 mg/ml ; 0.0056 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.72
Solubility	0.0437 mg/ml ; 0.000192 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.22 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.99

Application In Synthesis of [ 18442-22-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 18442-22-3 ]

[ 18442-22-3 ] Synthesis Path-Downstream 1~35

1
[ 18442-22-3 ]
[ 917-92-0 ]
[ 890840-81-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); copper(l) iodide; triphenylphosphine; at 140℃; for 0.333333h;Microwave irradiation;	Example 79C; A mixture of the product from Example 79B (979 mg, 4.33 mmol), tert-butylacetylene (3 mL, 24.4 mmol), CuI (166 mg, 0.872 mmol), triphenyl phosphine (304 mg, 1.16 mmol), and tris(dibenzylideneacetone)dipalladium(0) (789 mg, 0.862 mmol) was heated in triethylamine (8 mL) under microwave power at 140 for 20 min. Evaporation of the volatiles in vacuo, followed by silica gel chromatography, afforded Example 79C as a yellow oil, 741 mg (75%)

References: [1]Patent: US2006/128689,2006,A1 .Location in patent: Page/Page column 43.

2
[ 890840-78-5 ]
[ 18442-22-3 ]

Yield	Reaction Conditions	Operation in experiment
13%	In ethylene glycol; for 4h;Heating / reflux;	Example 79B; The product from Example 79A (7.935 g, 32.3 mmol) was refluxed in ethylene glycol for 4 h. The solution was then cooled to rt and poured into water. The mixture was extracted with ether, then the extracts were washed with water and brine. Concentration in vacuo, followed by silica gel chromatography (9:1 hexane-ethyl acetate to 65:35 hexane-ethyl acetate, eluent gradient), afforded Example 79B as a thick yellow oil, 979 mg (13%).

References: [1]Patent: US2006/128689,2006,A1 .Location in patent: Page/Page column 43.

3
[ 18386-03-3 ]
[ 18442-22-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With polyphosphoric acid; at 80℃; for 2h;	Weighed compound 7 (5g), added to a three-necked bottle, and weighed 50mL of polyphosphoric acid into a 100mL three-necked bottle.The reaction system was heated in an oil bath and stirred at 80 C for 2 hours. Lower the system temperature to room temperature,The reaction was quenched by adding 100 mL of water and stirring for 10 minutes, and extracted three times with 100 mL of ethyl acetate.The organic phases are combined, then the organic phase is washed with water and the organic phase washed with saturated sodium chloride.Dried over anhydrous sodium sulfate, filtered and concentrated, the crude product was purified by column chromatography (mobile phase:Ethyl acetate: petroleum ether = 1:3) was purified. 3.1 g (60%) of a yellow solid were obtained.
	With phosphorus pentachloride;aluminium chloride;	Example 30 7-Bromo-2,3-dihydro-4H-chromen-4-one 2.45 g (10 mmol) of the compound from Example 5 are added to 3.12 g (15.00 mmol) of phosphorus pentachloride. The mixture is stirred at room temperature for O min, resulting in a clear solution. After addition of 2.67 g (20 mmol) of aluminium chloride, the reaction mixture becomes solid. It is heated at 130 C. for 30 min and, after cooling, added to ice and extracted with ethyl acetate. The organic phase is washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulphate and, after removal of the solvent by distillation, purified by column chromatography on silica gel (V 8:2). Recrystallization from cyclohexane/pentane affords 0.78 g (34%) of colourless crystals. 1H-NMR (200 MHz, CDCl3, delta/ppm): 2.80 (t, 2H), 4.55 (t, 2H), 7.15 (dd, 1H), 7.25 (s, 1H), 7.71 (t, 1H). MS (EI POS): 226 [M+].
	With polyphosphoric acid; at 70℃; for 2h;Inert atmosphere;	Into a 3-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-(3-bromophenoxy)- propanoic acid (195 g, 795.69 mmol, 1.00 equiv), and PPA (2008 g). The reaction was stirred for 2 h at 70C in an oil bath, then slowly poured into 2 L of ice. The resulting solids were collected by filtration, and purified by Prep-SFC (Column, AD-H; mobile phase, (0284) methanol:MeCN=l: l; Detector, UV, 220, 254 nm) to give the title compound

With polyphosphoric acid; at 70℃; for 2h;Inert atmosphere;

Into a 3-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-(3-bromophenoxy)-propanoic acid (195 g, 795.69 mmol, 1.00 equiv), and PPA (2008 g). The reaction was stirred for 2 h at 70C in an oil bath, then slowly poured into 2 L of ice. The resulting solids were collected by filtration, and purified by Prep-SFC (Column, AD-H; mobile phase, methanol:MeCN=1:1; Detector, UV, 220, 254 nm) to give the title compound.

References: [1]Patent: CN108250058,2018,A .Location in patent: Paragraph 0235; 0242-0245.
[2]Patent: US2002/82264,2002,A1 .
[3]Patent: WO2017/95725,2017,A1 .Location in patent: Page/Page column 39.
[4]Patent: WO2017/95724,2017,A1 .Location in patent: Page/Page column 47.

4
[ 18442-22-3 ]
sodium hydrosulfide monohydrate [ No CAS ]
7-[4-(4-methoxytetrahydropyran-4-yl)thien-2-ylthio]chroman-4-one [ No CAS ]
[ 161385-95-1 ]

Yield	Reaction Conditions	Operation in experiment
73%		The 7-[4-(4-methoxytetrahydropyran-4-yl)thien-2-ylthio]chroman-4-one used as a starting material was obtained as follows: A solution of sodium hydrosulphide hydrate (8.88 g) in NMP (150 ml) was stirred and heated to 140 C. The mixture was partially evaporated under vacuum to remove the water. The mixture was cooled to 45 C. and a solution of <strong>[18442-22-3]7-bromochroman-4-one</strong> (12 g) in NMP (150 ml) was added dropwise. The mixture was stirred and heated to 50 C. for 30 minutes. The mixture was poured onto a mixture of ice and water and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated to give 7-mercaptochroman-4-one (7 g, 73%). A solution of the material so obtained in DMSO (20 ml) was stirred at ambient temperature for 16 hours. The mixture was poured onto a mixture of ice and water. The precipitate was isolated and dried.

References: [1]Patent: US5332757,1994,A .

Yield	Reaction Conditions	Operation in experiment
39%		A mixture of the product so obtained and 2N aqueous sodium hydroxide (100 ml) was stirred at ambient temperature. The precipitate was isolated and purified by column chromatography using a 4:1 mixture of petroleum ether and methylene chloride as eluent. There was thus obtained 7-bromochroman-4-one in 39% yield, m.p. 95-97C.

6
[ 18442-22-3 ]
[ 155650-73-0 ]

Yield	Reaction Conditions	Operation in experiment
64%		Using analogous procedures to those described in the portion of Example 2 which is concerned with the preparation of starting materials, <strong>[18442-22-3]7-bromochroman-4-one</strong> was converted in turn into:- <strong>[18442-22-3]7-bromochroman-4-one</strong> ethylene acetal in 64% yield;

References: [1]Patent: EP581464,1994,A1 .

7
[ 18442-22-3 ]
[ 945724-03-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With bromine; In tetrachloromethane; for 1.58333h;	lnter.med.iate 6; 3,3,7-fribromo-2,3-dihydro-4H-chromen-4-one.; To a vigorously stirring solution of 7-Bromo-2,3-dihydro-4W-chromen-4-oiotaie (20.0 g,88.1 mmoi) in CCI4 (400 mL) was added dropwise a solution of bromine (10 mL, 194 mmoi) in CCI4 {100 mL) over 45 minutes. The resulting solution was stirred for 50 minutes and CHCl3(100 mL) was added to the solution to dissolve the precipitate, The solution was washed with 10% NaHSO3 (75 mL), dried over Na2SC^ and evaporated to dryness to give the title compound (32,5 g, 86%) as a yellowish solid. LC/MS data; 302.9 (M-Br)* (Calculated for C9HsBr3O2 384.85). (calo. monoisotopic mass is 38171, calc. monoisotopio mass (M-Br)+= 302.9). 1H NMR data (DMSO-ddelta): 7.82 (d, 1H, J = 8.6 Hz, Ar-H), 7.51 (d, 1H, J = 2.0 Hz, Ar- H)1 7.42 (dd, 1H1 J1= 8.3, «4=1.7 Hz, Ar-H)1 5.02 (s, 2H, CH2).

References: [1]Patent: WO2007/88450,2007,A2 .Location in patent: Page/Page column 23.

8
[ 168759-60-2 ]
[ 18442-22-3 ]

Yield	Reaction Conditions	Operation in experiment
78%		A solution of diisobutylaluminum hydride in heptane (1.0 M, 60 mL, 60.0 mmol) was added dropwise to a solution of 7-bromo-4H-chromen-4-one (4.5 g, 20.0 mmol) in tetrahydrofuran at -78 C under an atmosphere of argon over a period of 30 minutes. After 30 minutes the reaction was quenched with a mixture of silica gel (10 g), and water (10 mL). The mixture was allowed to warm to room temperature and was filter through celite and the tetrahydrofuran was removed under reduced pressure. The residue was taken up in chloroform (100 mL) and washed with sodium hydroxide (IN, 25 mL) and dried over sodium sulfate. The mixture was filtered and the solvent was removed under reduced pressure. The residue was subjected to flash chromatography with eluant of dichloromethane. The product containing fractions were combined and the solvent was removed under reduced pressure to provide 7- bromochroman-4-one (3.57 g, 15.7 mmol, 78 %).
69%		Intermediate 5; 7-Bromo-2,3-dhydro-4W-chromen-4-one.;The solution of 7-Bromo-4H-chromen-4-one (26.0 g, 116 mmol) in absolute THF (500 mL) was stirred under argon for 1 h and then it was cooled to -80 0C. To a suspension formed a solution of diisobutylaluminum hydride 1M In heptane (173 mL, 173 mmol) was added during 30 minutes and the resulting mixture was stirred at -80 0C for additional 30 minutes. The solution was quenched by mixture of SiO2 (52 g) and H2O (52 mL), allowed to warm to 00C. Then SiO2 was filtered, washed with EtOAc and the solution was evaporated to dryness. The residue was dissolved in CHCI3 (400 mL), washed with 1 N NaOH (300 mL), dried over Na2SO4 and evaporated. The resulting solid was purified by column chromatography on SiO2 (63-100 mum, 1200 mL) in CHCI3 (80 - 100%) gradient in hexane to afford 101865-076 (18.1 g, 69%) as a pale yellow solid. LC/MS data: 226.9 V(M+Hf (Calculated for C8H7BrO2 227.06) (calc. monoisotopic mass is 225.96, calc. monoisotopic mass (M+Hf = 226.96). 1H NMR data (DMSO-d6): 7.66 (d, 1H1 J=8.3 Hz, Ar-H), 7.33 (d, 1H, J=2.0 Hz, Ar-H), 7.25 (dd, 1H, ^=8.3 Hz1 J2=L 7 Hz, Ar-H), 4.56 (t 2H, CH2 , J=6.6 Hz)1 2.80 (t, 2H, CH2 , J=S,6 Hz).
51.7%	With diisobutylaluminium hydride; In tetrahydrofuran; at -78℃; for 0.5h;	A solution of XXV-3 (2.9 g, 12.9 mmol) in THF (10 mL) was cooled to -78 C., DIBAl-H (24 mL, 24 mmol) was added and the resulting solution was stirred at -78 C. for 30 min., Then sat.NH4Cl was added to quench the reaction, extracted with EA, washed with brine, dried over Na2SO4 and concentrated, the residue was purified by flash chromatography (PE/EA=1/1) to give XXV-4 (1.5 g, yield: 51.7%) as a yellow solid.

	With diisobutylaluminium hydride; In tetrahydrofuran; chloroform; toluene;	Example 14c; step 5: A solution of 7-bromo-4H-chromen-4-one (26 g, 116 mmol) in dry THF (500 mL) under nitrogen for 1 hr, cooled to -80 C., and 173 mL of diisobutylaluminium hydride (2M in Toluene) was added over 30 minutes. The reaction was stirred at the same temperature for 30 min, quenched with a SiO2 (52 g)/water (52 mL) suspension, and allowed to warm to 0 C. The solution was filtered, the SiO2 washed with EtOAc, and the combined filtrate was concentrated to dryness. The residue was dissolved in CHCl3 (400 mL), washed with 1N NaOH (300 mL), dried over Na2SO4 and concentrated. Purification by chromatography on SiO2 (60-120 mesh) EtOAc/Pet ether (gradient elution 0-15%) afforded 7-bromochroman-4-one 18.1 g (69%) a pale yellow solid. LCMS 229.0 (M+2H); 1H NMR (DMSO-d6) 7.64-7.67 (d, 1H), 7.32 (s, 1H), 7.22-7.25(d, 1H), 4.53-4.57 (t, 2H), 2.76-2.80 (t, 2H).
	With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78℃; for 1.5h;Inert atmosphere;	To a solution of compound 1D (32.6 g, 145.5 mmol) in THF (600 mL) was added DIBAL (1 M in toluene, 437 mL, 437 mmol) dropwise under nitrogen at -78 for 30 minutes. The mixture was allowed to stir at -78 for 1 hour, then the reaction mixture was poured into 500 mL of 1 M aq. HCl, and extracted with ethyl acetate. The organic extract was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue obtained was purified using flash column chromatography on silica gel (petroleum ether: ethyl acetate 20: 1 to provide compound 1E as a solid. 1H-NMR (CDCl3, 400 MHz) : delta 7.72 (d, J 8.0 Hz, 1H) , 7.13-7.17 (m, 2H) , 4.52 (t, J 6.4 Hz, 1H) , 2.79 (d, J 6.4 Hz, 1H).

References: [1]Patent: WO2012/68234,2012,A2 .Location in patent: Page/Page column 629; 630.
[2]Patent: WO2007/88450,2007,A2 .Location in patent: Page/Page column 22.
[3]Journal of Medicinal Chemistry,2016,vol. 59,p. 10228 - 10243.
[4]Patent: US2014/200215,2014,A1 .Location in patent: Paragraph 1148; 1150.
[5]Patent: US2009/202478,2009,A1 .
[6]Patent: WO2018/32467,2018,A1 .Location in patent: Page/Page column 39; 40.

9
[ 491-37-2 ]
[ 18442-22-3 ]

Yield	Reaction Conditions	Operation in experiment
74%		7-Bromo-4-chromanone. Into a round bottom flask kept at 0 C., AlCl3 (0.533 g, 3.99 mmol) and, 5 mL of CH2Cl2 was added. The reaction system was put under nitrogen and stirred for about 7 minutes before adding 10 mL of a CH2Cl2 solution of 4-chromanone (0.296 g, 1.99 mmol). After the reaction mixture was stirred for 10 minutes, 10 mL of Br2 (0.352 g, 2.20 mmol) was added and, the reaction mixture was stirred at room temperature for an hour. At the end of this period of time, the reaction mixture was poured into 30 mL of ice-water and, the product was extracted 3 times from the aqueous phase with EtOAc. The resultant organic phase was washed once with brine and dried under Na2SO4. After the solvent was evaporated, the solid formed was filtered and dried to obtain 0.361 g (1.51 mmol) of the product (93% pure) in a 74% yield. 1H NMR (300 MHz, CDCl3, delta): 7.90 (dd, J=2.6, 0.3 ArH, 1H,), 7.47 (dd, J=8.8, 2.5, Ar, 1H,), 6.82 (dd, J=8.8, 0.2, Ar, 1H), 4.48 (t, J=6.5, C2, 2H), 2.75 (t, J=6.5, C2, 2H).

References: [1]Patent: US2009/76076,2009,A1 .Location in patent: Page/Page column 24-25.

10
[ 1016736-70-1 ]
[ 18442-22-3 ]
5-bromo-2,3-dihydro-4H-chromen-4-one [ No CAS ]

References: [1]Australian Journal of Chemistry,2010,vol. 63,p. 1582 - 1593.

11
[ 591-20-8 ]
[ 18442-22-3 ]
5-bromo-2,3-dihydro-4H-chromen-4-one [ No CAS ]

References: [1]Australian Journal of Chemistry,2010,vol. 63,p. 1582 - 1593.
[2]Tetrahedron Letters,2011,vol. 52,p. 4824 - 4826.
[3]Patent: EP2518064,2012,A1 .

12
[ 18386-03-3 ]
[ 18442-22-3 ]
5-bromo-2,3-dihydro-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentaoxide;methanesulfonic acid; at 80℃; for 0.05h;	Diphosphorus pentoxide (17.9 g) was added to methanesulfonic acid (82.0 mL), and the compound (15.4 g) obtained in (EXAMPLE 2) <Step 1> was then added to the mixture at 80C. After stirring for 3 minutes, the reaction solution was poured onto ice and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium hydrogencarbonate aqueous solution and brine, and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluate; n-hexane : ethyl acetate = 100:0 to 75:25) to give a mixture (9.8 g) of the title compounds (2-2-a and 2-2-b) as a purple solid.

References: [1]Australian Journal of Chemistry,2010,vol. 63,p. 1582 - 1593.
[2]Patent: EP2518064,2012,A1 .Location in patent: Page/Page column 42.

13
[ 1493-13-6 ]
[ 1016736-70-1 ]
[ 18442-22-3 ]
5-bromo-2,3-dihydro-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a 25 mL 2-necked round-bottomed flask, equipped with thermocouple and nitrogen inlet, was charged 3-aryloxypropanenitriles 2a-2j (12.6 mmol) in 5 equiv of TFA(4.86 mL, 63.0 mmol) solution. To the resulting solution was slowly added 1.5 equiv of TfOH (1.67 mL, 17.7 mmol) at 0-5 C. The resulting solution was stirred at 0 C for 5 h, and then at ambient temperature for 16-24 h until the conversion of the reaction was >99%. The reaction mixture was cooled to 0 C. Then, 2 equiv of water (0.41 mL, 25.2 mmol) was added dropwise at 0-10 C. The resulting solution was stirred at room temperature for 1-5 h. The reaction mixture was transferred to a separation funnel and diluted with toluene (20 mL) and water (10 mL). After phase separation, the aqueous layer was extracted with toluene (6 mL × 1). The combined organic layers were washed with water (9 mL × 1) and concentrated. The pure 4-chromanones 3a, 3b, 3d, 3f, 3h, and 3i obtained by crystallization of their corresponding crude products in isopropanol (IPA) and the pure chromanones 3c, 3-4e, 3g and 3j were obtained by Biotage chromatographic purification (EtOAc/hexanes from 10% to 80%).

References: [1]Tetrahedron Letters,2011,vol. 52,p. 4824 - 4826.

14
[ 30186-18-6 ]
[ 18442-22-3 ]

References: [1]Patent: WO2012/68234,2012,A2 .
[2]Patent: US2014/200215,2014,A1 .
[3]Journal of Medicinal Chemistry,2016,vol. 59,p. 10228 - 10243.
[4]Patent: WO2018/32467,2018,A1 .

15
[ 18442-22-3 ]
[ 1180671-97-9 ]

References: [1]Patent: WO2012/68234,2012,A2 .

16
[ 18442-22-3 ]
[ 27407-19-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; for 0.25h;Reflux;	A solution of sodium acetate (3.86 g, 47.2 mmol) in water (30 mL) was added to a solution of <strong>[18442-22-3]7-bromochroman-4-one</strong> (3.57 g, 15.7 mmol), and hydroxylamine hydrochloride (1.64 g, 23.5 mmol) in ethanol (70 mL). The mixture was heated at reflux for 15 minutes. The mixture was cooled to room temperature and diluted with water (50 mL). The resulting solid was isolated by filtration, washed with water (50 mL) and azeotroped with toluene to provide (2s, )-7-bromochrornan-4-one oxime (3.5 g, 14.5 mmol, 92 %).
77%	With hydroxylamine hydrochloride; sodium acetate; In ethanol; at 30 - 100℃; for 116h;	Example 56A <strong>[18442-22-3]7-bromochroman-4-one</strong> oxime <strong>[18442-22-3]7-bromochroman-4-one</strong> (CAS 18442-22-3, 0.523 g, 2.303 mmol) was treated with hydroxylamine hydrochloride (0.192 g, 2.76 mmol) and sodium acetate (0.227 g, 2.76 mmol) in ethanol (5 mL). The reaction was stirred at 30 C for 16 hours, then at 100 C for 100 hours. The solvent was removed under a stream of nitrogen and the crude material was triturated with water, filtered, washed with water, and dried to provide the title compound (0.429 g, 1.772 mmol, 77 % yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 11.36 (s, 1H), 7.70 (d, J = 8.1 Hz, 1H), 7.17 - 7.09 (m, 2H), 4.20 (t, J = 6.2 Hz, 2H), 2.83 (t, J = 6.2 Hz, 2H).
	With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; for 0.416667h;Reflux;	Step F3a. A mixture of <strong>[18442-22-3]7-bromochroman-4-one</strong> (2.50 g, 11.01 mmol) and NaOAc (2.71g, 33.04 mmol) in EtOH (20 mL) and 0 (20 mL) was treated with hydroxylamine hydrochloride (1.15g, 16.52 mmol) under reflux for 25 minutes before 0 (50 ml) was added. After being cooled at 0 C for 2 hours, the yellow solid precipitate was collected by filtration to give the crude desired compound (2.2 g, 83 %), which was used directly in next step.

References: [1]Patent: WO2012/68234,2012,A2 .Location in patent: Page/Page column 629; 630.
[2]Patent: WO2016/69757,2016,A1 .Location in patent: Page/Page column 180.
[3]Patent: WO2015/17382,2015,A1 .Location in patent: Page/Page column 87.

17
[ 18442-22-3 ]
[ 1180671-95-7 ]

References: [1]Patent: WO2012/68234,2012,A2 .

18
[ 18442-22-3 ]
[ 1180672-01-8 ]

References: [1]Patent: WO2012/68234,2012,A2 .

19
[ 18442-22-3 ]
[ 1180672-04-1 ]

References: [1]Patent: WO2012/68234,2012,A2 .

20
[ 945724-02-7 ]
[ 18442-22-3 ]

References: [1]Patent: WO2012/68234,2012,A2 .
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 10228 - 10243.

21
[ 18442-22-3 ]
[ 1396777-41-5 ]

Yield	Reaction Conditions	Operation in experiment
100%		A solution of <strong>[18442-22-3]7-bromochroman-4-one</strong> (340 mg, 1.5 mmol) and methanesulfonic acid (3 mL, 23.0 mmol) in DCM was cooled to 0 C. and treated with NaN3 (146 mg, 2.25 mmol) portionwise, while maintaining the internal temperature below 5 C. The reaction was then stirred at 0 C. for 4 h. At completion, the reaction was slowly neutralized with 8 N aq. NaOH, then diluted with DCM (20 mL) and water (20 mL). The layers were separated and the organics were dried over MgSO4, filtered and evaporated to afford 8-bromo-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (370 mg, 100% yield). MS (EI) m/z=242.1 [M+1]+.

References: [1]Patent: US2012/225857,2012,A1 .Location in patent: Page/Page column 22.

22
[ 18442-22-3 ]
[ 18385-82-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 20℃; for 0.5h;	[0331j To a solution of <strong>[18442-22-3]7-bromochroman-4-one</strong> (1.63 g, 7.2 mmol, 1.0 equiv) in MeOH (10 mL) was added NaBH4 (545 mg, 14.4 mmol, 2.0 equiv) and then stirred at room temperature for 30 minutes. After evaporation of the solvent, the residue was purified by silica gel column (EtOAc/hexane=1 :2) to give 7-bromochroman-4-ol (1.61 g, yield: 98%) as a white solid. ESIMS (M+H-1 8) : 211.0. ?H NMR (400 MHz, CDC13) 5: 7.17 (d, J = 8.0 Hz, 1H), 7.05-7.0 1 (m, 2H), 4.76-4.73 (m, 1H), 4.27-4.24 (m, 2H) 2.14-1.99 (m, 2H).
	With methanol; sodium tetrahydroborate; at 20℃; for 0.5h;	NaBH4 (166 mg, 4.40 mmol) was added to a solution of <strong>[18442-22-3]7-bromochroman-4-one</strong> (2.00 g, 8.80 mmol) in MeOH (45 mL) at r.t. After 30 minutes, the reaction was quenched by the addition of 1% aqueous HCl (100 mL) and DCM (100 mL). The organic layer was removed and the aqueous layer was extracted with DCM (2 x 100 mL). The combined organic fractions were dried with Na2SO4 and concentrated. The crude product was used in the subsequent step without further purification.

References: [1]Patent: WO2015/89337,2015,A1 .Location in patent: Paragraph 0331.
[2]Patent: US2013/18055,2013,A1 .Location in patent: Paragraph 0317-0318.
[3]Patent: WO2017/58821,2017,A1 .Location in patent: Page/Page column 135; 136.

23
[ 876149-55-2 ]
[ 18442-22-3 ]

References: [1]Patent: US2014/200215,2014,A1 .
[2]Patent: WO2018/32467,2018,A1 .

24
[ 18442-22-3 ]
[ 1620075-07-1 ]

References: [1]Patent: US2014/200215,2014,A1 .

25
[ 18442-22-3 ]
[ 1620075-08-2 ]

References: [1]Patent: US2014/200215,2014,A1 .

26
[ 18442-22-3 ]
[ 7677-24-9 ]
[ 1620075-06-0 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 24h;	To a solution of XXV-4 (2.27 g, 10 mmol) was added the iodine (76.2 mg, 0.3 mmol), TMSCN (1.5 g, 15 mmol) in DCM (20 mL). The resulting solution was stirred at rt for another 24 hs. Then the NaHSO3 (aq.) was added and extracted with DCM. The organic lays was evaporated in vacuum to afford the crude XXV-5, which was used to next step without purification.
	With zinc(II) iodide; In diethyl ether; at 20℃; for 17h;	A mixture of <strong>[18442-22-3]7-bromochroman-4-one</strong> (3 g, 13.21 mmol) in ether (6 ml) was treated with trimethylsilanecarbonitrile (1.991 ml, 15.86 mmol) followed by zinc iodide (0.084 g, 0.264 mmol) and the reaction mixture was stirred at room temperature for 17 horns. The mixture was diluted with ether (15 mL), treated with activated carbon (30 mg), and filtered through a bed of diatomaceous earth. The filtrate was concentrated and purified by silica gel columnchromatography to give the title compound.

References: [1]Patent: US2014/200215,2014,A1 .Location in patent: Paragraph 1148; 1151.
[2]Patent: WO2016/44770,2016,A1 .Location in patent: Page/Page column 781.

27
[ 18442-22-3 ]
[ 7677-24-9 ]
[ 1616267-30-1 ]

Yield	Reaction Conditions	Operation in experiment
900 mg		TMS-cyanide (2.2 mL, 17.6 mmol) was added to a solution of<strong>[18442-22-3]7-bromochroman-4-one</strong> (2.0 g, 8.8 mmol) in toluene (20 mL). Zinc iodide (20 mg) was added, and the reaction was stirred at 60 oc for 16 hours. The solution was cooled to rt and diluted with THF (10 mL). This was added to a mixture oflithium aluminum hydride (670 mg, 17.6 mmol) in THF (20 mL), and the reaction mixture was heated at 42 oc for 2 h. The reaction was cooled tort. EtOAc (5 mL) was slowly added, and the reaction stirred 30min. Water (1 mL) and then 5N NaOH (1 mL) were slowly added, and the reaction stirred 1 h. The reaction mixture was diluted with EtOAc (30 mL), dried (MgS04), filtered through Celite, and concentrated to give 1.8 g (79%) yellow oil.[00375] The intermediate was taken up in toluene (20 mL). 4N HCl in dioxane (10 mL) was added, and the reaction was heated at reflux under a Dean-Stark condenser for 2 h. The solution was concentrated in vacuo and taken up in EtOAc. The solid was collected by filtration, and was then dissolved in sat. NaHC03 and extracted (3X) with EtOAc. Organics were dried (Na2 S04) and concentrated to give 900 mg (54%) of the titlecompound as a yellow oil. 1H NMR (300 MHz, CD30D): 8 3.98 (2H, s), 4.84-4.87 (2H,m), 6.06 (1H, t, J = 3.6 Hz), 7.01 (1H, d, J = 1.8 Hz), 7.13 (1H, dd, J = 1.8, 8.4 Hz), 7.18 (1H, d, J = 8.4 Hz).

References: [1]Patent: WO2014/100818,2014,A1 .Location in patent: Paragraph 00374; 00375.

28
[ 18442-22-3 ]
[ 1616267-32-3 ]

References: [1]Patent: WO2014/100818,2014,A1 .

29
[ 18442-22-3 ]
[ 1616267-33-4 ]

References: [1]Patent: WO2014/100818,2014,A1 .

30
[ 18442-22-3 ]
[ 1616267-34-5 ]

References: [1]Patent: WO2014/100818,2014,A1 .

31
[ 18442-22-3 ]
[ 1616267-45-8 ]

References: [1]Patent: WO2014/100818,2014,A1 .

32
[ 18442-22-3 ]
[ 1616267-46-9 ]
[ 1616267-47-0 ]

References: [1]Patent: WO2014/100818,2014,A1 .

33
[ 18442-22-3 ]
[ 768-35-4 ]
[ 1616267-48-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃;	To a solution of 6-bromo-3,4-dihydro-2H-chromen-4-one (1.5 g, 6.6 mmol), 3- fluorophenylboronic acid (1.39 g, 9.9 mmol) and sodium carbonate (2.1 g, 19.8 mmol) indioxane (20 mL) and water (1 mL) was added Pd(PPh3)4 (382 mg, 0.3 mmol) at rt. The solution was heated at 100 o C overnight. The reaction was filtered, concentrated, and purified by silica gel chromatography (PE/EtOAc/DCM = 10:1:2) to give 1.4 g (88%) of the title compound as a white solid. 1H NMR (300 MHz, CDCh): 8 2.86 (2H, t, J = 6.6Hz), 4.60 (2H, t, J= 6.6 Hz), 7.11-7.14 (1H, m), 7.18 (1H, d, J= 1.5 Hz), 7.23-7.29 (2H, m), 7.32-7.45 (2H, m), 7.98 (1H, d, J = 8.1 Hz).

References: [1]Patent: WO2014/100818,2014,A1 .Location in patent: Paragraph 00457.

34
[ 18442-22-3 ]
[ 6746-94-7 ]
[ 1616267-57-2 ]

Yield	Reaction Conditions	Operation in experiment
88%		To a solution of<strong>[18442-22-3]7-bromochroman-4-one</strong> (2.0 g, 8.8 mmol) in DMF (10 mL)was added Cui (380 mg, 1.7 mmol), Pd(PPh3)Clz (540 mg, 0.8 mmol) and triethylamine (5 mL) under nitrogen at rt. The suspension was warmed to 100 oc and then cyclopropylacetylene (1.1 g, 17.6 mmol) was added dropwise. The mixture was stirred at100 oc under nitrogen for 2 h. The reaction mixture was cooled to rt, poured into water,and extracted with EtOAc. Organics were separated and washed with brine, dried(Na2S04), and concentrated. The residue was purified by silica gel chromatography to give 1.65 g (88%) of the title compound as a tan solid. 1H NMR (300 MHz, CDCh): 80.83-0.93 (4H, m), 1.44-1.49 (1H, m), 2.79 (2H, t, J = 6.6 Hz), 4.52 (2H, t, J = 6.6 Hz),6.96-7.00 (2H, m), 7.79 (1H, d, J = 7.8 Hz). [M+H] calc'd for C14H1zO, 213; found 213.

References: [1]Patent: WO2014/100818,2014,A1 .Location in patent: Paragraph 00483.

35
[ 18442-22-3 ]
[ 6746-94-7 ]
[ 1616267-58-3 ]

References: [1]Patent: WO2014/100818,2014,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 18442-22-3 ]

Bromides

A302766 [55580-08-0]

7-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Similarity: 0.94

A154179 [1199782-67-6]

5-Bromochroman-4-one

Similarity: 0.91

A307269 [49660-57-3]

6-Bromochroman-4-one

Similarity: 0.90

A165204 [130200-01-0]

7-Bromo-2,2-dimethylchroman-4-one

Similarity: 0.90

A140747 [141106-23-2]

8-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Similarity: 0.89

Ketones

A302766 [55580-08-0]

7-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Similarity: 0.94

A154179 [1199782-67-6]

5-Bromochroman-4-one

Similarity: 0.91

A307269 [49660-57-3]

6-Bromochroman-4-one

Similarity: 0.90

A165204 [130200-01-0]

7-Bromo-2,2-dimethylchroman-4-one

Similarity: 0.90

A140747 [141106-23-2]

8-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Similarity: 0.89

Related Parent Nucleus of
[ 18442-22-3 ]

Other Aromatic Heterocycles

A302766 [55580-08-0]

7-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Similarity: 0.94

A154179 [1199782-67-6]

5-Bromochroman-4-one

Similarity: 0.91

A307269 [49660-57-3]

6-Bromochroman-4-one

Similarity: 0.90

A165204 [130200-01-0]

7-Bromo-2,2-dimethylchroman-4-one

Similarity: 0.90

A140747 [141106-23-2]

8-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Similarity: 0.89

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H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 18442-22-3

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