Phenylboronic Acid → (R)-4-methyl-3-{4-[4-(3-methyl-5-phenylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one

HRID 1804406Notes

Reaction equation

HRID 1804406 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:29])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[C@H:26]([CH3:27])[CH2:25][O:24][C:23]4=[O:28])=[CH:18][CH:17]=3)=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH3:27][C@@H:26]1[CH2:25][O:24][C:23](=[O:28])[N:22]1[C:19]1[CH:20]=[CH:21][C:16]([C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[C:4]([CH3:29])=[CH:3][C:2]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:7][N:6]=3)[CH2:9][CH2:10]2)=[O:15])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 67381057HCID 67381057, compound

Product 1

HCID 58484867(R)-4-methyl-3-{4-[4-(3-methyl-5-phenylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one

Procedure

By reaction and treatment in the same manner as in Preparation Example 186 and using the obtained (R)-3-{4-[4-(5-bromo-3-methylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-4-methyloxazolidin-2-one (535 mg) and phenylboronic acid (183 mg), (R)-4-methyl-3-{4-[4-(3-methyl-5-phenylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one was obtained. The obtained compound was dissolved in ethyl acetate (10 mL), 4N hydrogen chloride/ethyl acetate (0.3 mL) was added, and the precipitate was collected by filtration to give the title compound (475 mg).

Workup

  1. customBy reaction and treatment in the same manner
  2. customas in Preparation Example 186

Sources & evidence

ORD record
ord-f91c86fc0db9404781402912cc3fad6d
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

Loading…