Sodium borohydride → (4-Chloro-2-methoxy-8-methyl-3-(3-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol

HRID 1507321Notes

Reaction equation

HRID 1507321 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([CH3:22])[CH:10]=[C:11]([C:14]([C:16]3[N:20]([CH3:21])[CH:19]=[N:18][CH:17]=3)=[O:15])[CH:12]=2)[N:7]=[C:6]([O:23][CH3:24])[C:5]=1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1>CO>[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([CH3:22])[CH:10]=[C:11]([CH:14]([C:16]3[N:20]([CH3:21])[CH:19]=[N:18][CH:17]=3)[OH:15])[CH:12]=2)[N:7]=[C:6]([O:23][CH3:24])[C:5]=1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:33])[F:35])[CH:27]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118005951(4-chloro-2-methoxy-8-methyl-3-(3-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone2×

Product 1

HCID 118006194(4-Chloro-2-methoxy-8-methyl-3-(3-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.016 g, 0.422 mmol) was added in one portion to a suspension of (4-chloro-2-methoxy-8-methyl-3-(3-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone (0.1 g, 0.211 mmol, Intermediate 15: step d) in MeOH (3 mL). The mixture was stirred at room temperature overnight, then filtered, rinsing the solids with MeOH and H2O. The solid product was dried under reduced pressure to provide the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 8.08 (s, 1H), 7.57-7.69 (m, 1H), 7.41-7.53 (m, 4H), 7.30-7.41 (m, 1H), 6.76 (s, 1H), 5.94-6.15 (m, 1H), 4.35 (s, 2H), 4.09 (s, 3H), 3.60 (s, 3H), 2.67 (s, 3H), 2.58 (m, 1H). MS (EI) 476 [M+H]+.

Workup

  1. filtrationfiltered
  2. washrinsing the solids with MeOH and H2O
  3. customThe solid product was dried under reduced pressure

Sources & evidence

ORD record
ord-749d0cddd8db47afa56dc65011b4afea
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Reaction notes

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