1-(5-Bromo-2-fluorophenyl)pyrrolidin-2-one → 1-{2-Fluoro-5-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]phenyl}pyrrolidin-2-one

HRID 1180256Notes

Reaction equation

HRID 1180256 reaction equation
[F:1][C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:11])([CH3:10])[CH3:9].Br[C:16]1[CH:17]=[CH:18][C:19]([F:28])=[C:20]([N:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])[CH:21]=1>>[F:28][C:19]1[CH:18]=[CH:17][C:16]([C:12]2[N:4]3[CH:5]=[CH:6][C:7]([C:8]([OH:11])([CH3:10])[CH3:9])=[C:2]([F:1])[C:3]3=[N:14][CH:13]=2)=[CH:21][C:20]=1[N:22]1[CH2:26][CH2:25][CH2:24][C:23]1=[O:27]

Participants

3

Reactant 2

HCID 179648331-(5-Bromo-2-fluorophenyl)pyrrolidin-2-oneHCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 104068981-{2-Fluoro-5-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]phenyl}pyrrolidin-2-oneYield 31%

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 1-(5-bromo-2-fluorophenyl)pyrrolidin-2-one as described in Example 6 to give 1-{2-fluoro-5-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]phenyl}pyrrolidin-2-one as a pale yellow solid (114 mg, 31%): m/z (ES+) 372 [MH+].

Sources & evidence

ORD record
ord-294d6a9afff24ea980afe73cece2538b
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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