Borane;tetrahydrofuran → HCID 71114332, compound

HRID 331041Notes

Reaction equation

HRID 331041 reaction equation
B.C1COCC1.[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][CH2:13][N:14]2[C:17](=O)[C:18]([F:21])([F:20])[F:19])=[CH:10][CH:9]=1>C1COCC1>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][CH2:13][N:14]2[CH2:17][C:18]([F:21])([F:19])[F:20])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 86720292HCID 86720292, compound

Product 1

HCID 71114332HCID 71114332, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of BH3.THF (1M in THF) (6.12 mL, 6.12 mmol) was added to a solution of 1-(6-bromoindolin-1-yl)-2,2,2-trifluoroethanone (D74) (900 mg, 3.06 mmol) in dry THF (2.0 mL) stirred at 0° C. The mixture was then heated at reflux for overnight (ca. 16 hours). The reaction mixture was quenched with aqueous ammonium chloride, and was partitioned between water (25 mL) and ethyl acetate (100 mL). The aqueous phase was separated and extracted with additional ethyl acetate (100 mL). The organic extracts were combined, washed with brine (25 mL), dried with anhydrous magnesium sulfate, filtered and evaporated to dryness. The residues were purified on silica eluting with cyclohexane and ethyl acetate (0-100%). The appropriate fractions were combined and evaporated to dryness producing title compound (670 mg). LCMS (A): m/z (M+H)+ 280/282, C10H9BrF3N requires 279/281 (acidic).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for overnight (ca. 16 hours)
  3. customThe reaction mixture was quenched with aqueous ammonium chloride
  4. customwas partitioned between water (25 mL) and ethyl acetate (100 mL)
  5. customThe aqueous phase was separated
  6. extractionextracted with additional ethyl acetate (100 mL)
  7. washwashed with brine (25 mL)
  8. dry with materialdried with anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residues were purified on silica eluting with cyclohexane and ethyl acetate (0-100%)
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-a5ae3ece761a4085888998b95c19d00b
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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