Boron tribromide → HCID 68679641, compound

HRID 1443271Notes

Reaction equation

HRID 1443271 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:32])([CH3:31])[CH2:10][C:11]([CH:17]=[N:18][C:19]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]3[C:20]=2[CH:21]=[N:22][C:23]([CH3:30])=[N:24]3)([OH:16])[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:29][C:26]1[CH:27]=[CH:28][C:19]([NH:18][CH:17]2[C:6]3[C:5](=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=3)[C:9]([CH3:31])([CH3:32])[CH2:10][C:11]2([C:12]([F:14])([F:15])[F:13])[OH:16])=[C:20]2[C:25]=1[N:24]=[C:23]([CH3:30])[N:22]=[CH:21]2

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 17989163HCID 17989163, compound

Product 1

HCID 68679641HCID 68679641, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60 mg (0.133 mmol) of 4-(3-methoxyphenyl)-1,1,1-trifluoro-2-{[8-fluoro-2-methylquinazolin-5-ylimino]-methyl}-4-methylpentan-2-ol is mixed with 1.3 ml of a 1 M solution of boron tribromide in dichloromethane while being cooled in an ice bath. After 45 minutes of stirring at room temperature, the reaction mixture is mixed with ice, and saturated sodium bicarbonate solution is added drop by drop until a pH of 8 is reached. The cold bath is removed, and the mixture is stirred vigorously for 15 minutes. After extraction with ethyl acetate, the combined organic extracts are washed with water and then with brine. After drying, the solvent is spun off, and the residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). Ultimately, 19.5 mg (33.5%) of the desired compound is obtained.

Workup

  1. temperaturewhile being cooled in an ice bath
  2. additionis added drop by drop until a pH of 8
  3. customThe cold bath is removed
  4. stirringthe mixture is stirred vigorously for 15 minutes
  5. extractionAfter extraction with ethyl acetate
  6. washthe combined organic extracts are washed with water
  7. customAfter drying
  8. customthe residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8dfc7bad5193426699c5cc35e3feac46
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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