Boron tribromide → HCID 10620412, compound

HRID 865255Notes

Reaction equation

HRID 865255 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([NH:18][C:19](=[O:27])[C:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22])[CH:6]=[CH:7][C:8]=1[S:9]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([NH:18][C:19](=[O:27])[C:20]([OH:26])([CH3:25])[C:21]([F:23])([F:24])[F:22])[CH:6]=[CH:7][C:8]=1[S:9]([C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 25134Boron tribromide3×HCID 10739955HCID 10739955, compound

Product 1

HCID 10620412HCID 10620412, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a stirred suspension of N-[3-methoxy-4-(4-pyridylsulfonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (1.05 g, 2.6 mmol) in dry methylene chloride (30 mL) was added boron tribromide (10.4 mL of a 1.0 M solution of boron tribromide in methylene chloride, 10.4 mmol). The resulting solution was stirred at reflux for 2 hours. An additional 5 mL of 1.0M boron tribromide solution in methylene chloride was added and the reaction stirred overnight at room temperature. The reaction mixture was diluted with methylene chloride (50 mL) and washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo to yield an oil. Purification by flash column chromatography (20% v/v methanol in ethyl acetate) yielded the title propanamide as a white solid (0.18 g, 18%); mp 188°-189° C. 1H-NMR (250 MHz, d6-DMSO): 1.54 (s, 3H, CH3) 7.35 (d, 1H, J=9.0 Hz, aromatic) 7.51 (s, 1H, OH) 7.61 (s, 1H, aromatic) 7.77 (d, 2H, J=5.5 Hz, aromatic) 7.84 (d, 1H, J=8.9 Hz, aromatic) 8.83 (d, 2H, J=5.5 Hz, aromatic) 10.26 (s, 1H, NH) 11.04 (s, 1H, ArOH). MS (CI, CH4): 391 (M+1).

Workup

  1. temperatureat reflux for 2 hours
  2. stirringthe reaction stirred overnight at room temperature
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield an oil
  7. customPurification by flash column chromatography (20% v/v methanol in ethyl acetate)

Sources & evidence

ORD record
ord-315927f34027424eaa5a73ee8f5d239d
Source dataset
uspto-grants-1996_10
Patent number
US05565477

Reaction notes

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