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Sodium borohydride → 1-{5-Chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-piperazin-1-yl]-pyridin-3-yl}-ethanol

HRID 730820
Notes
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Reaction equation

HRID 730820 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:27](=[O:29])[CH3:28])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:10][CH2:9]1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]([OH:29])[CH3:28])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23]([F:25])([F:26])[F:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:12][CH2:13]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 104774141-(5-chloro-6-(4-(5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)piperazin-1-yl)pyridin-3-yl)ethanone

Product 1

HCID 117188331-{5-Chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-piperazin-1-yl]-pyridin-3-yl}-ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-{5-chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-piperazin-1-yl]-pyridin-3-yl}-ethanone (0.3 g, 0.71 mmol, Example 97e) in MeOH (20 mL) was added portionwise NaBH4 (0.037 g, 1.0 mmol, Aldrich) with stirring at 0° C. The reaction mixture was stirred at 0° C. for 30 min, quenched with 20 mL of satd. aq. NaHCO3, and diluted with EtOAc (50 mL). The organic phase was separated, washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from 1:1 EtOAc/hexane mixture to give the title compound as a white foam. MS (ESI, pos. ion) m/z: 426 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 30 min
  2. customquenched with 20 mL of satd
  3. additionaq. NaHCO3, and diluted with EtOAc (50 mL)
  4. customThe organic phase was separated
  5. washwashed with brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from 1:1 EtOAc/hexane mixture

Sources & evidence

ORD record
ord-9943509d6bc44fd0a0f3d13e6bed9062
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582761B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes