Sodium Methoxide → (4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanol

HRID 2172533Notes

Reaction equation

HRID 2172533 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:13][C:14]([C:21]3[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[N:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[CH2:15][N:16]=2)=[CH:8][C:7]=1[Br:35])(=O)C.C[O-].[Na+]>CO.C(OC)(C)(C)C>[F:34][C:31]([F:32])([F:33])[C:23]1[CH:22]=[C:21]([C:14]2([C:17]([F:18])([F:19])[F:20])[CH2:13][C:12]([C:9]3[CH:10]=[CH:11][C:6]([CH2:5][OH:4])=[C:7]([Br:35])[CH:8]=3)=[N:16][CH2:15]2)[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[N:24]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 866646224-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromobenzyl acetate

Product 1

HCID 86664623(4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromophenyl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4-{3-[2,6-bis(trifluoromethyl)pyridin-4-yl]-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl}-2-bromobenzyl acetate (0.5 g) and Sodium methoxide (0.005 g) in MeOH (10 ml) were stirred at room temperature for 30 minutes. The mixture was diluted with t-BuOMe, and washed with brine, and the organic layer was dried over MgSO4. After the solvent was evaporated under reduced pressure, the targeted product was obtained (0.4 g).

Workup

  1. washwashed with brine
  2. dry with materialthe organic layer was dried over MgSO4
  3. customAfter the solvent was evaporated under reduced pressure
  4. customthe targeted product was obtained (0.4 g)

Sources & evidence

ORD record
ord-303f3c3c5e1547f1b80d80542b6b8f1f
Source dataset
uspto-grants-2015_06
Patent number
US09055749B2

Reaction notes

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