Sodium borohydride → HCID 67410607, compound

HRID 1987138Notes

Reaction equation

HRID 1987138 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:14](=[O:15])[C:13]3[CH:16]=[C:17]([C:20](=[O:24])[CH:21]([F:23])[F:22])[CH:18]=[CH:19][C:12]=3[CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1>CO>[Cl:3][C:4]1[CH:5]=[C:6]2[CH:14]([OH:15])[C:13]3[CH:16]=[C:17]([CH:20]([OH:24])[CH:21]([F:22])[F:23])[CH:18]=[CH:19][C:12]=3[CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86609784HCID 86609784, compound

Product 1

HCID 67410607HCID 67410607, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (15 mg, 0.4 mmol) was added to a slurry of 3-chloro-7-(difluoroacetyl)-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (60 mg, 0.19 mmol) in methanol (2 mL) at room temperature. The mixture was stirred for 20 minutes at which time it was quenched via the dropwise addition of 2N aqueous hydrochloric acid. Once gas evolution ceased, the solvent was removed in vacuo. The resulting residue was taken up in ethyl acetate and poured into saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate three times. The combined organics were dried over magnesium sulfate, filtered, concentrated in vacuo, and purified via flash chromatography (silica, 0-50% ethyl acetate/hexanes) to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 8.37 (s, 1H), 8.14 (s, 1H), 7.87 (d, 1H), 7.36 (m, 3H), 7.15 (dd, 1H), 5.82 (tt, 1H), 5.19 (s, 1H), 4.83-4.78 (m, 1H), 3.30 (s, 2H).

Workup

  1. customwas quenched via the dropwise addition of 2N aqueous hydrochloric acid
  2. customthe solvent was removed in vacuo
  3. additionpoured into saturated aqueous sodium bicarbonate
  4. extractionThe aqueous layer was extracted with ethyl acetate three times
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified via flash chromatography (silica, 0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f8aec92fb27e46bca8fb4ea7c8a1c1ea
Source dataset
uspto-grants-2009_06
Patent number
US07550478B2

Reaction notes

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