Acetic Acid → (5-bromo-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)thiophen-3-yl)(4-chlorophenyl)methanol

HRID 2401983Notes

Reaction equation

HRID 2401983 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[N:11]=[CH:10][N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:8]=2)=[C:4]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[O:19])[CH:3]=1.O1CCCC1.[BH4-].[Li+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(=O)=O.CC(C)=O.CCOC(C)=O>[Br:1][C:2]1[S:6][C:5]([C:7]2[N:11]=[CH:10][N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:8]=2)=[C:4]([CH:18]([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[OH:19])[CH:3]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8028Tetrahydrofuran2×HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 66749271(5-bromo-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)thiophen-3-yl)(4-chlorophenyl)methanone

Product 1

HCID 66749509(5-bromo-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)thiophen-3-yl)(4-chlorophenyl)methanol

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 18522661Acetone cardiceSolvent

Procedure

To a solution of {5-bromo-2-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-3-thienyl}(4-chlorophenyl)methanone (11.81 g, 26.08 mmol) in tetrahydrofuran (300 mL, 4000 mmol) was added lithium tetrahydroborate (52.17 mmol, 52.17 mmol) in tetrahydrofuran (26 mL, 320 mmol) under argon. The mixture was stirred at rt for 3 h and then cooled down in dry ice-acetone bath. Acetic acid (7.1 mL, 120 mmol) was added. The mixture was stirred for 5 min and saturated aqueous sodium bicarbonate solution was added, followed by EtOAc. The organic layer was separated and washed with brine, then dried over sodium sulfate. The solvent was removed and the residue was purified by column chromatography to afford (5-bromo-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)thiophen-3-yl)(4-chlorophenyl)methanol as a white powder (11.2, 94.2%). LCMS: (FA) ES+ 454.0, 456.0

Workup

  1. stirringThe mixture was stirred for 5 min
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e0e22d710f9a4fd9bdc844dabdb82b18
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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