Sodium borohydride → HCID 59525813, compound

HRID 386002Notes

Reaction equation

HRID 386002 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([F:12])[C:3]=1[C:13]1[S:17][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25](=[O:28])[CH2:26][F:27])[N:20]=2)=[C:15]([C:29]([NH2:31])=[O:30])[CH:14]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([C:8]([OH:11])([CH3:9])[CH3:10])[CH:5]=[C:4]([F:12])[C:3]=1[C:13]1[S:17][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([OH:28])[CH2:26][F:27])[N:20]=2)=[C:15]([C:29]([NH2:31])=[O:30])[CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86646277HCID 86646277, compound

Product 1

HCID 59525813HCID 59525813, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a dry flask, 5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(fluoroacetyl)pyridin-2-yl]amino}thiophene-3-carboxamide (33.6 mg, 0.08 mmol) was taken up in methanol (0.75 ml) at room temperature. Sodium borohydride (6 mg, 0.15 mmol) was added in small portions and the reaction mixture was stirred at room temperature overnight. The reaction was quenched with aqueous sodium bicarbonate and extracted three times with ethyl acetate. All organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford the title compound.

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-482c1a158f1a45a8a4542dbcfe5fc95e
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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