885267-36-7|6-Bromo-3-fluoropyridine-2-carbaldehyde| Ambeed

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Quality Control of [ 885267-36-7 ] Purity: 98% SDS Specification

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Product Details of [ 885267-36-7 ]

CAS No. :	885267-36-7
Formula :	C₆H₃BrFNO
M.W :	204.00
SMILES Code :	O=CC1=NC(Br)=CC=C1F
MDL No. :	MFCD07781224
InChI Key :	BFBRCFKSFRYJGE-UHFFFAOYSA-N
Pubchem ID :	16414238

Safety of [ 885267-36-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 885267-36-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	37.28
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.96 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.28
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	1.77
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.22
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.	1.0
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	2.61
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.77

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.6
Solubility	0.515 mg/ml ; 0.00252 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.	-2.02
Solubility	1.96 mg/ml ; 0.00961 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	-3.11
Solubility	0.158 mg/ml ; 0.000776 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.	-6.29 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	2.0 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)	1.8

Application In Synthesis of [ 885267-36-7 ]

* 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 [ 885267-36-7 ]

[ 885267-36-7 ] Synthesis Path-Downstream 1~35

1
[ 110-89-4 ]
[ 885267-36-7 ]
[ 1228660-65-8 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

2
[ 110-89-4 ]
[ 885267-36-7 ]
[ 1228659-68-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

3
[ 110-91-8 ]
[ 885267-36-7 ]
[ 1228660-63-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

4
[ 39093-93-1 ]
[ 885267-36-7 ]
[ 1228660-62-5 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

5
[ 885267-36-7 ]
[ 1338056-05-5 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.
[2]Biochemical Pharmacology,2018,vol. 152,p. 129 - 142.

6
[ 885267-36-7 ]
[ 1228659-42-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.
[2]Biochemical Pharmacology,2018,vol. 152,p. 129 - 142.

7
[ 885267-36-7 ]
[ 1228660-00-1 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.
[2]Biochemical Pharmacology,2018,vol. 152,p. 129 - 142.

8
[ 885267-36-7 ]
[ 104223-69-0 ]
[ 1228660-68-1 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

9
[ 885267-36-7 ]
[ 104223-69-0 ]
[ 1228659-45-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

10
[ 885267-36-7 ]
[ 626-56-2 ]
[ 1228660-64-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

11
[ 885267-36-7 ]
[ 626-56-2 ]
[ 1228659-43-5 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

12
[ 885267-36-7 ]
3,3-difluoropiperidine hydrochloride [ No CAS ]
[ 1228660-67-0 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

13
[ 885267-36-7 ]
3,3-difluoropiperidine hydrochloride [ No CAS ]
[ 1228659-44-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7350 - 7362.

14
[ 885267-36-7 ]
[ 411235-57-9 ]
[ 1374649-99-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 22h;Inert atmosphere; Sonographic reaction;	R-5 (2.20 g, 10.78 mmol) is combined with R-8 (1.20 g, 14.02 mmol), tribasic potassium phosphate (8.01 g, 37.75 mmol) and tricyclohexylphosphine (0.30 g, 1.08 mmol) and diluted with toluene (40 ml) and water (2 ml). The palladium acetate is added (0.24 g, 1.08 mmol) and the mixture is sonicated for five minutes and then degassed with nitrogen. The reaction is warmed to 100C for 22 hours, cooled to ambient temperature and poured into water. The product is extracted into ethyl acetate and the organics are dried with MgS04, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 5-40% ethyl acetate in heptane as the eluent to afford R-9.

References: [1]Patent: WO2012/61169,2012,A1 .Location in patent: Page/Page column 46; 47.

15
[ 885267-36-7 ]
[ 1374649-94-1 ]

References: [1]Patent: WO2012/61169,2012,A1 .

16
[ 885267-36-7 ]
[ 1374649-64-5 ]

References: [1]Patent: WO2012/61169,2012,A1 .

17
[ 1310531-65-7 ]
[ 885267-36-7 ]
[ 1374650-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	With Oxone; In water; N,N-dimethyl-formamide; at 20℃; for 0.5h;	To a solution of 1-1 (500 mg, 1.94 mmol) in DMF (20 mL) is added R-5 (396 mg, 1.94 mmol) followed by a solution of oxone (1.19 g, 1.94 mmol) in water (6 ml) at room temperature. The solution is stirred for 30 minutes and poured into water (75 ml) and saturated aqueous sodium thiosulfate (75 ml). The product is extracted into ethyl acetate and the organics are dried with MgS04, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 10% MeOH in CH2CI2 as the eluent to afford R-6.

References: [1]Patent: WO2012/61169,2012,A1 .Location in patent: Page/Page column 52.

18
[ 4276-09-9 ]
[ 885267-36-7 ]
[ 1401163-28-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example 73A (2R)-2-[(6-bromo-3-fluoropyridin-2-yl)methyl]amino}-3-methylbutan-1-ol <strong>[885267-36-7]6-bromo-3-fluoropicolinaldehyde</strong> (4.0 g, 19.61 mmol) and (R)-2-amino-3-methylbutan-1-ol (2.281 mL, 20.59 mmol) were dissolved in methanol (100 mL) and stirred at ambient temperature for 1 hour and 15 minutes. Sodium borohydride (0.742 g, 19.61 mmol) was added and the mixture was stirred for another 1 hour and 30 minutes. The volume of the reaction mixture was reduced, and the mixture was quenched with 200 mL 1.0 N NaOH, and extracted with 200 mL dichloromethane (2*). The organic phase was extracted with 1.0 N HCl and partitioned. The aqueous phase was separated, neutralized with 3.0 N NaOH, extracted with EtOAc, organic phase separated and washed with brine. The organic phase was dried over Na2SO4, filtered, and concentrated to obtain the title compound as an orange solid. MS (ESI+) m/z 291.0 (M+H); 1H NMR (300 MHz, DMSO-d6) delta 7.69 (t, J=8.8, 1H), 7.60 (dd, J=8.6, 3.7, 1H), 4.42 (t, J=5.2, 1H), 3.92-3.75 (m, 2H), 3.43 (dt, J=10.7, 4.8, 1H), 2.34-2.24 (m, 1H), 2.08 (s, 1H), 1.87-1.71 (m, 1H), 0.83 (dd, J=8.5, 6.9, 6H).

References: [1]Patent: US2012/245124,2012,A1 .Location in patent: Page/Page column 46.

19
6-(trifluoromethyl)-3-pyridinylboronic acid [ No CAS ]
[ 885267-36-7 ]
[ 1401162-75-1 ]

Yield	Reaction Conditions	Operation in experiment
69.5%	tetrakis(triphenylphosphine) palladium(0); at 80℃;Inert atmosphere;	Example 28A5-fluoro-6'-(trifluoromethyl)-2,3'-bipyridine-6-carbaldehydeNitrogen was bubbled through a mixture of 6-(trifluoromethyl)pyridin-3-ylboronic acid (3.74 g, 19.61 mmol), <strong>[885267-36-7]6-bromo-3-fluoropicolinaldehyde</strong> (4.0 g, 19.61 mmol), Pd(Ph3P)4 (0.340 g, 0.294 mmol) was added and nitrogen was bubbled for 10 minutes, and the reaction mixture was heated overnight at 80 C. EtOAc (300 mL) was added and the mixture was washed with water (300 mL) and brine (300 mL), dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on a Grace Reveleris 80 g column, eluted with 0-40% EtOAc in Heptane (30 mL/min) to provide the title compound (3.681 g, 13.62 mmol, 69.5% yield). MS (ESI+) m/z 303.0 (M+H+MeOH); 1H NMR (300 MHz, DMSO-d6) delta 10.15 (s, 1H), 9.50 (d, J=2.0, 1H), 8.82-8.75 (m, 1H), 8.58 (dd, J=8.9, 3.7, 1H), 8.23-8.13 (m, 1H), 8.10 (d, J=8.3, 1H).

References: [1]Patent: US2012/245124,2012,A1 .Location in patent: Page/Page column 39.

20
[ 885267-36-7 ]
[ 1401162-74-0 ]