Sodium triacetoxyborohydride → {6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetic acid ethyl ester

HRID 532844Notes

Reaction equation

HRID 532844 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[C:16]([N:17]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[CH3:24])[CH3:2].[C:26]1([N:32]2[CH:36]=[CH:35][C:34]([CH:37]=O)=[N:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[C:16]([N:17]2[CH2:23][CH2:22][CH2:21][N:20]([CH2:37][C:34]3[CH:35]=[CH:36][N:32]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:33]=3)[CH2:19][CH2:18]2)=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[CH3:24])[CH3:2]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 134324761-Phenyl-1H-pyrazole-3-carbaldehydeHCID 59366177(8-[1,4]Diazepan-1-yl-6-methyl-quinolin-7-yloxy)-acetic acid ethyl ester

Product 1

HCID 59366193{6-Methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]-quinolin-7-yloxy}-acetic acid ethyl esterYield 57.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of (8-[1,4]diazepan-1-yl-6-methyl-quinolin-7-yloxy)-acetic acid ethyl ester (600 mg, 1.75 mmol), 1-Phenyl-1H-pyrazole-3-carbaldehyde (300.8 mg, 1.75) and NaBH(OAc)3 (408 mg, 1.92 mmol) in DCE (5 ml) was stirred at rt for 3 hrs. The reaction was then diluted with DCE (20 ml), filtered, and purified by flash column chromatography on silica gel to give the desired product (500 mg, 57%). MS (ES) m/z 500.2 (M+H+).

Workup

  1. filtrationfiltered
  2. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-4a232e139c964bfdb8e4eb8968899491
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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