206347-30-0|7-Bromo-2,3-dihydrobenzofuran| Ambeed

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Quality Control of [ 206347-30-0 ] Purity: 98% SDS Specification

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Product Details of [ 206347-30-0 ]

CAS No. :	206347-30-0
Formula :	C₈H₇BrO
M.W :	199.05
SMILES Code :	BrC1=C(OCC2)C2=CC=C1
MDL No. :	MFCD09266210
Boiling Point :	No data available
InChI Key :	VGOUXHRZQNPOPY-UHFFFAOYSA-N
Pubchem ID :	22571869

Safety of [ 206347-30-0 ]

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

Computational Chemistry of [ 206347-30-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	43.49
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	9.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.23
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	2.62
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.38
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.	2.49
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	3.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.59

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.17
Solubility	0.135 mg/ml ; 0.000678 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.	-2.46
Solubility	0.684 mg/ml ; 0.00344 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	-3.54
Solubility	0.0567 mg/ml ; 0.000285 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.	-5.65 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	2.0
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)	1.79

Application In Synthesis of [ 206347-30-0 ]

* 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 [ 206347-30-0 ]

[ 206347-30-0 ] Synthesis Path-Downstream 1~34

1
[ 206347-32-2 ]
[ 206347-30-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0℃; for 1h;	Synthesis of 7-Bromo-2,3-dihydro-benzofuran A solution of 2.5M n-BuLi (13.0 ml, 32.5 mmol) was added to a solution of 1,3-dibromo-2-(2-bromo-ethoxy)-benzene (11.5, 32.0 mmol) in 115 ml of THF and 28 ml of hexane at -78 C. over 30 mins. The reaction was continued at -78 C. for 30 minutes, then warmed to 0 C. The mixture was poured into water (100 ml) and the aqueous phase was extracted with ether. The combined organic layers were dried over Na2SO4, filtered, and concentrated to give a pale yellow oil. Silica gel chromatography using a gradient of ethyl acetate in hexanes to give 7-bromo-2,3-dihydro-benzofuran as colorless needles (5.00 g, 78%). 1H NMR (500 MHz, DMSO-d6) delta 7.27(dd, 1 Hz, 8 Hz, 1H), 7.20 (dd, 1 Hz, 7.5 Hz, 1H), 6.75 (t, 7.8 Hz, 1H), 4.59 (t, 9 Hz, 2H), 3.28 (t, 8.8 Hz, 2H).
	With n-butyllithium; In tetrahydrofuran; hexane; at -80℃;	1-(2,3-Dihydrobenzofuran-7-yl)piperazine (C7i); In detail, for the synthesis of compound C7i 2,6-dibromophenole (29 mmol) (C8a; R4-R6 = H) is mixed with 1,2-dibromoethane (29 mmol) (r = 1) unter basic aqueous conditions (NaOH) and heated at reflux for 18 hrs. The resulting monoalkylation product can be solved in THF/hexane (4/1), cooled to -80 C and then, a solution of 2,5 M butyllithium (18mmol) in hexane is added dropwise (17.1 mmol). The cyclisation product 7-bromo-2,3-dihydrobenzofurane (4 mmol) (C8b; r = 1) can be suspended together with NaOtBu (20 mmol), Pd2(dba)3 (2 mol%), BINAP (2 mol%) and piperazine (8 mmol) in 5 ml dry toluene and heated at 117C for 6 hrs to get the product.
	With n-butyllithium; In tetrahydrofuran; at -100℃;	2. Synthesis of 2,3-dihydrobenzofuran-7-sulfonyl chloride; n-Butyllithium (23 mmol) was added dropwise to a solution of 1,3-dibromo-2-(2-bromoethoxy)benzene (21.8 mmol) in tetrahydrofuran (100 mL) at -100 C. and the reaction mixture was maintained for 30 min. n-Butyllithium (23 mmol) was added dropwise and the reaction mixture was maintained at -100 C. for an additional 60 min. Sulfur dioxide (43.8 mmol) was added and the reaction mixture was maintained for 2 h between -100 and -85 C. The reaction mixture was diluted with hexane (100 mL) and the precipitated solids were collected by filtration. The solid was suspended in dichloromethane (100 mL) at 0 C. and N-chlorosuccinamide (24.6 mmol) was added in several batches. The reaction mixture was maintained for 60 min at 0 C. and was diluted with dichloromethane (100 mL). The reaction mixture was washed with (2 M) sodium hydrogen sulfate (2×150 mL) and brine (3×100 mL), was dried (sodium sulfate), and was concentrated. The residue was purified by Flash chromatography (1/50 ethyl acetate/petroleum ether) to provide 2,3-dihydrobenzofuran-7-sulfonyl chloride in 51% yield as a light yellow solid. Data: 1H NMR: (CDCl3) delta 3.35 (t, 2H), 4.92 (t, 2H), 6.96 (t, 1H), 7.54 (s, 1H), 7.64 (d, 1H). LC/MS (ES) m/z 283 [C13H18N2O3S+H]+.

References: [1]Tetrahedron Letters,1998,vol. 39,p. 2219 - 2222.
[2]Patent: US2006/30583,2006,A1 .Location in patent: Page/Page column 104.
[3]Patent: EP1972628,2008,A1 .Location in patent: Page/Page column 56-57.
[4]Patent: US2010/16297,2010,A1 .Location in patent: Page/Page column 34.

2
[ 206347-30-0 ]
[ 57260-71-6 ]
[ 846037-41-0 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine; In toluene; for 16h;Heating / reflux;	[1289] A first intermediate compound 4-(2,3-Dihydro-benzofuran-7-yl)-piperazine-1-carboxylic acid tert-butyl ester, was produced as follows: A solution of bis-(dibenzylideneacetone)palladium(0) (4.92 g, 0.16 mol) and toluene (2500 ml) was degassed with nitrogen for 15 minutes. (Note: Degassing was continued during each addition. Time between additions was 15 minutes.) Then added was tri-o-tolylphosphine (4.92 g, 0.16 mol) then sodium t-butoxide (53.8 g, 0.56 mol) then Boc-piperazine (86.8 g, 0.47 mol) then a solution of <strong>[206347-30-0]7-bromo-2,3-dihydro-benzofuran</strong> (79.6 g, 0.40 mol, prepared according to Tetrahedron Lett. 1998, 39, 2219) in toluene (100 ml). The reaction mixture was stirred at reflux for 16 h. By TLC, all starting material had been consumed. The cooled reaction mixture was filtered over a pad of Celite. The filtrate was concentrated under reduced pressure and the residue was triturated with ethyl acetate in heptane (50%). The insoluble material was filtered off and that filtrate was concentrated under reduced pressure. The crude residue was purified by flash column chromatography using ethyl acetate in heptane (50%) to give 46.4 g (38% yield) of the first intermediate compound as a tan solid.

References: [1]Patent: US2005/43309,2005,A1 .Location in patent: Page/Page column 104.
[2]Tetrahedron Letters,1998,vol. 39,p. 2219 - 2222.

3
[ 1692-15-5 ]
[ 206347-30-0 ]
[ 794465-11-5 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176.

4
[ 206347-30-0 ]
2-[4-(2,3-dihydro-benzofuran-7-yl)-3,6-dihydro-2<i>H</i>-pyridin-1-yl]-5-fluoro-indan-1-ol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176.

5
[ 206347-30-0 ]
(1S,2S)-2-[4-(2,3-Dihydro-benzofuran-7-yl)-piperidin-1-yl]-5-fluoro-indan-1-ol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176.

6
[ 206347-30-0 ]
4-(2,3-dihydro-benzofuran-7-yl)-1-(5-fluoro-1-oxo-indan-2-yl)-pyridinium; bromide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176.

7
[ 608-33-3 ]
[ 206347-30-0 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 2219 - 2222.

8
[ 206347-30-0 ]
[ 98205-73-3 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 2219 - 2222.

9
[ 104-15-4 ]
[ 206347-30-0 ]
[ 856679-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	With methanesulfonic acid; phosphorus pentoxide; at 20℃;	INTERMEDIATE 78 7-Bromo-5- [ (4-methylphenyl) sulfonyl]-2, 3-dihydro-l-benzofuran 7-Bromo-1, 2-dihydrobenzofuran (64 mg, 0.3 mmol; Intermediate 77) and para- toluensulfonic acid monohydrate (62 mg, 0.3 mmol) were mixed and then a 1: 10 mixture (by weight) of methanesulfonic and phosphorous pentoxide (1 mL) was added. The resultant mixture was stirred over night at room temperature and was then poured onto ice/water. The obtained crystalline material was filtered and dried to give 120 mg of the title product.'H NMR (400 MHz, CDC13) 8 2.40 (s, 3 H), 3.33 (t, 2 H), 4.73 (t, 2 H), 7.29 (d, 2 H), 7.65 (d, 1 H), 7.79 (d, 2 H), 7.89 (d, 1 H); GC-MS (EI+) for C15Hl3BrSO3 m/z 354 (M+H) +.

References: [1]Patent: WO2005/58858,2005,A1 .Location in patent: Page/Page column 169.

10
[ 206347-32-2 ]
[ 496-16-2 ]
[ 206347-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0℃;Cooling with ethanol-dry ice;	INTERMEDIATE 77 7-Bromo-2, 3-dihydrobenzofuran* A solution of 2- (2, 6-dibromphenoxy) ethyl bromide (1.08 g, 3 mmol; Intermediate 76) in a mixture of THF (12 mL) and hexane (3 mL) was cooled in a ethanol/dry ice bath for 30 min. n-BuLi in hexane (2 mL of 1.5 M solution) was added dropwise over 15 min. The reaction mixture was stirred at-78 C for another 30 min after which time the bath was allowed to slowly warm to 0 C. The mixture was poured onto water and extracted with diethyl ether (2x100 mL). The combined extract was dried and concentrated to give a pale brown oil (0.5 g) containing the product contaminated with approximately 25 % 2,3- dihydrobenzofuran. This material was used as such for further synthesis but could if necessary be purified by flash chromatography [eluent : hexane- EtOAc/hexane (5: 95) ]. 'H NMR (400 MHz, CDC13) 8 3.30 (t, 2 H), 4.65 (t, 2 H), 6.71 (t, 1 H), 7.11 (dd, 1 H), 7.25 (dd, 1 H). *Previously reported in Tetrahedron Lett. 1998,39, 2219-2222.

References: [1]Patent: WO2005/58858,2005,A1 .Location in patent: Page/Page column 168-169.

11
[ 608-33-3 ]
[ 206347-30-0 ]
4,5-Bis-(4-chloro-phenyl)-2-(2,3-dihydro-benzofuran-7-yl)-4,5-dihydro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 21 4,5-Bis-(4-chloro-phenyl)-2-(2,3-dihydro-benzofuran-7-yl)-4,5-dihydro-1H-imidazole was prepared from <strong>[206347-30-0]7-bromo-2,3-dihydro-benzofuran</strong> (prepared from 2,6-dibromo-phenol using the procedure reported by Thomas, G. H. et al. Tetrahedron Lett. 1998, 39, 2219-22) and meso-1,2-bis-(4-chloro-phenyl)-ethane-1,2-diamine in an analogous manner as described in example 20. HR-MS (ES, m/z) calculated for C23H19N2OCl2 [(M+H)+] 409.0869, observed 409.0871.

References: [1]Patent: US6617346,2003,B1 .

12
[ 206347-30-0 ]
[ 111538-45-5 ]
Trans-2-[4-(2,3-dihydrobenzofuran-7-yl)piperid-1-yl]-5-fluoroindan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 31 Trans-2-[4-(2,3-dihydrobenzofuran-7-yl)piperid-1-yl]-5-fluoroindan-1-ol Prepared using, in succession, the methods described in Examples 18, 19 and 23, but using <strong>[206347-30-0]7-bromo-2,3-dihydrobenzofuran</strong> in Step 1 of Example 18, and using 2-bromo-5-fluoro-indan-1-one in Step 2 of Example 18. The melting point (MK) of the title compound is 215-217 C.

References: [1]Patent: US5958927,1999,A .

13
[ 110-85-0 ]
[ 206347-30-0 ]
[ 98205-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 117℃; for 6h;	1-(2,3-Dihydrobenzofuran-7-yl)piperazine (C7i); In detail, for the synthesis of compound C7i 2,6-dibromophenole (29 mmol) (C8a; R4-R6 = H) is mixed with 1,2-dibromoethane (29 mmol) (r = 1) unter basic aqueous conditions (NaOH) and heated at reflux for 18 hrs. The resulting monoalkylation product can be solved in THF/hexane (4/1), cooled to -80 C and then, a solution of 2,5 M butyllithium (18mmol) in hexane is added dropwise (17.1 mmol). The cyclisation product <strong>[206347-30-0]7-bromo-2,3-dihydrobenzofuran</strong>e (4 mmol) (C8b; r = 1) can be suspended together with NaOtBu (20 mmol), Pd2(dba)3 (2 mol%), BINAP (2 mol%) and piperazine (8 mmol) in 5 ml dry toluene and heated at 117C for 6 hrs to get the product.

References: [1]Patent: EP1972628,2008,A1 .Location in patent: Page/Page column 56-57.

14
[ 206347-30-0 ]
[ 470453-91-9 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4149 - 4160.

15
[ 206347-30-0 ]
[ 953408-82-7 ]

Yield	Reaction Conditions	Operation in experiment
		2. Synthesis of 2,3-dihydrobenzofuran-7-sulfonyl chloride; n-Butyllithium (23 mmol) was added dropwise to a solution of 1,3-dibromo-2-(2-bromoethoxy)benzene (21.8 mmol) in tetrahydrofuran (100 mL) at -100 C. and the reaction mixture was maintained for 30 min. n-Butyllithium (23 mmol) was added dropwise and the reaction mixture was maintained at -100 C. for an additional 60 min. Sulfur dioxide (43.8 mmol) was added and the reaction mixture was maintained for 2 h between -100 and -85 C. The reaction mixture was diluted with hexane (100 mL) and the precipitated solids were collected by filtration. The solid was suspended in dichloromethane (100 mL) at 0 C. and N-chlorosuccinamide (24.6 mmol) was added in several batches. The reaction mixture was maintained for 60 min at 0 C. and was diluted with dichloromethane (100 mL). The reaction mixture was washed with (2 M) sodium hydrogen sulfate (2×150 mL) and brine (3×100 mL), was dried (sodium sulfate), and was concentrated. The residue was purified by Flash chromatography (1/50 ethyl acetate/petroleum ether) to provide 2,3-dihydrobenzofuran-7-sulfonyl chloride in 51% yield as a light yellow solid. Data: 1H NMR: (CDCl3) delta 3.35 (t, 2H), 4.92 (t, 2H), 6.96 (t, 1H), 7.54 (s, 1H), 7.64 (d, 1H). LC/MS (ES) m/z 283 [C13H18N2O3S+H]+.

References: [1]Patent: US2010/16297,2010,A1 .Location in patent: Page/Page column 34.

16
[ 73183-34-3 ]
[ 206347-30-0 ]
7-( 4,4,5,5-tetra methyl-[1,3,2]dioxaborola n-2-yl)-2,3-dihydro-benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80℃; for 8h;Inert atmosphere;	Compound <strong>[206347-30-0]7-bromobenzodihydrofuran</strong> (0.4 g, 2 mmol), bis(pinacolato)diboron (0.78 g, 3 mmol) and anhydrouspotassium acetate (0.4 g, 4 mmol) were suspended in dimethyl sulfoxide (5 mL) and then [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.16 g, 0.2 mmol) was added. The reaction mixture was replacedwith nitrogen threetimes to remove the oxygen inside the system and then heated at 80C for 8 hours. The reaction was cooled to roomtemperature, diluted with ice water (100 mL) and extracted with ethyl acetate (50 mL 3 3). The combined organic phaseswere washed successively with water (50 mL 3 3) and brine (50 mL),dried over anhydrous sodium sulfate, filtered, andthe filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography(petroleum ether: ethyl acetate = 30: 1) to delivercompound 3-c (0.29 g, yield: 56%).1H-NMR (400MHz, CDCl3) delta: 7.53 (d, J=8Hz, 1H), 7.27 (d, J=8Hz, 1H), 6.83 (t, J=8Hz, 1H), 4.63 (t, J=8.8Hz, 1H), 3.16(t, J=8.8Hz, 1H), 1.36 (s, 12H) ppm.
56%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80℃; for 8h;Inert atmosphere;	The compound <strong>[206347-30-0]7-bromobenzodihydrofuran</strong> (0.4 g, 2 mmol), bis(pinacolato)diboron (0.78 g, 3 mmol) and anhydrous potassium acetate (0.4 g, 4 mmol) were suspended in dimethyl sulfoxide (5 mL), and [1,1'-bis (diphenylphosphino)ferrocene]dichloropalladium (0.16 g, 0.2 mmol) was added. The reaction solution was purged with nitrogen gas for three times to remove the oxygen contained in the system and heated at 80 C. for 8 hours. The reaction was cooled to room temperature, diluted with ice water (100 mL) and extracted with ethyl acetate (50 mL3). The combined organic phase was washed with water (50 mL3) and brine (50 mL) successively, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate=30:1) to give compound 2-b (0.29 g, yield 56%). 1H-NMR (400 MHz, CDCl3) delta: 7.53 (d, J=8 Hz, 1H), 7.27 (d, J=8 Hz, 1H), 6.83 (t, J=8 Hz, 1H), 4.63 (t, J=8.8 Hz, 1H), 3.16 (t, J=8.8 Hz, 1H), 1.36 (s, 12H) ppm

References: [1]Patent: EP3287463,2018,A1 .Location in patent: Paragraph 0121; 0122.
[2]Patent: US2018/208604,2018,A1 .Location in patent: Paragraph 0148-0150.

17
[ 206347-30-0 ]
7-(2,3-dihydro-1-benzofuran-7-yl)-N-[5-methyl-4-(piperidin-4-yl)-2-isopropoxyphenyl]-6-methylthieno[3,2-d]pyrimidin-2-amine [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

18
[ 206347-30-0 ]
7-(2,3-dihydro-1-benzofuran-7-yl)-N-(2-methoxy-4-(piperidin-4-yl)phenyl)-6-methylthieno[3,2-d]pyrimidin-2-amine [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

19
[ 206347-30-0 ]
C₁₅H₁₁ClN₂OS [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .
[2]Patent: US2018/208604,2018,A1 .

20
[ 206347-30-0 ]
C₃₂H₃₆N₄O₄S [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

21
[ 206347-30-0 ]
C₃₄H₄₀N₄O₄S [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

22
[ 206347-30-0 ]
C₃₅H₄₂N₄O₄S [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

23
[ 206347-30-0 ]
7-(2,3-dihydro-1-benzofuran-7-yl)-N-[4-(piperidin-4-yl)-2-isopropoxyphenyl]-6-methylthieno[3,2-d]pyrimidin-2-amine [ No CAS ]

References: [1]Patent: EP3287463,2018,A1 .

24
[ 206347-30-0 ]
N-[7-(2,3-dihydro-1-benzofuran-7-yl)-6-methylthieno[3,2-d]pyrimidinyl-2-yl]-1-(piperidinyl-4-yl)-1H-pyrazol-4-amine [ No CAS ]