Sodium cyanoborohydride → 6-Fluoro-5-[4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]-2-methylquinoline

HRID 2220249Notes

Reaction equation

HRID 2220249 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([CH3:21])[CH2:12][C:13]([OH:20])([C:16]([F:19])([F:18])[F:17])[CH:14]=O)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[NH2:23][C:24]1[C:33]([F:34])=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28]([CH3:35])=[N:29]2.C([BH3-])#N.[Na+]>>[F:34][C:33]1[C:24]([NH:23][CH2:14][C:13]([OH:20])([C:16]([F:17])([F:19])[F:18])[CH2:12][C:11]([C:4]2[C:5]3[O:9][CH2:8][CH2:7][C:6]=3[CH:10]=[C:2]([F:1])[CH:3]=2)([CH3:21])[CH3:22])=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[C:28]([CH3:35])[CH:27]=[CH:26]2

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 128968136-Fluoro-2-methylquinolin-5-amineHCID 441849894-(2,3-Dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal

Product 1

HCID 117056816-Fluoro-5-[4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]-2-methylquinoline

Procedure

Analogously to Example 1, the corresponding imine is produced starting from 250 mg of 4-(2,3-dihydro-5-fluoro-7-benzofuranyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentanal and 138 mg of 5-amino-6-fluoro-2-methylquinoline. After reaction with sodium cyanoborohydride, the title compound is obtained.

Sources & evidence

ORD record
ord-e995160c861b4fe6a861255f0124edc0
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Reaction notes

Loading…