Boron tribromide → HCID 58860854, compound

HRID 1350320Notes

Reaction equation

HRID 1350320 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-2d00340531364a2285aa3b2d6a715eb1
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

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