Boron tribromide → HCID 58860854, compound

HRID 729728Notes

Reaction equation

HRID 729728 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](=[CH:22]\[CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)/[C:14]([NH:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)=[O:15])=[CH:9][CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](=[CH:22]\[CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)/[C:14]([NH:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)=[O:15])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10315480HCID 10315480, compound

Product 1

HCID 58860854HCID 58860854, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

BBr3 (2.5 mL of a 1.0M solution in CH2Cl2, 2.5 mmol) was added to a stirred solution of (E)-2-(4-methoxyphenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylacrylamide (EXAMPLE 13, 340 mg, 984 μmol) in anhydrous CH2Cl2 (20 mL) at −78° C. After 1 h, the mixture was allowed to warm to 20° C. over a period of 24 h. CH2Cl2 (100 mL) was added, then the mixture was washed with H2O (20 mL) and brine (20 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (CH2Cl2-MeOH, 50:1) furnished the title compound: RTB=1.27 min; m/z (ES+)=331.0 [M+H]+.

Workup

  1. washthe mixture was washed with H2O (20 mL) and brine (20 mL)
  2. dry with materialbefore being dried (MgSO4)
  3. filtrationFiltration, solvent evaporation, and column chromatography (CH2Cl2-MeOH, 50:1)

Sources & evidence

ORD record
ord-42e46162948b4f16800788b122c1fb68
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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