Boron tribromide → HCID 67240265, compound

HRID 1949365Notes

Reaction equation

HRID 1949365 reaction equation
C[O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[C:18]4[S:22][C:21]([N:23]5[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]5)=[N:20][C:19]4=[O:30])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[C:5]([C:33]([F:36])([F:35])[F:34])[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[C:18]4[S:22][C:21]([N:23]5[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]5)=[N:20][C:19]4=[O:30])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[C:5]([C:33]([F:36])([F:35])[F:34])[CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67241306HCID 67241306, compound

Product 1

HCID 67240265HCID 67240265, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-[1-(4-methoxy-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-(4-methyl-piperazin-1-yl)-thiazol-4-one (32 mg, 0.062 mmol) in CH2Cl2 (1 mL) was added 0.4 mL of 1M BBr3 at −78° C. The mixture was stirred for 2 h at −78° C., then warmed up to room temperature. It was quenched with aqueous MeOH and NaHCO3 solution, extracted with EtOAc. The combined organic extracts were evaporated and the residue was purified by flash column chromatography on silica gel (0-100% gradient CH2Cl2/EtOAc, followed by 10% MeOH/EtOAc) to afford the title compound (30 mg, 96%).

Workup

  1. temperaturewarmed up to room temperature
  2. customIt was quenched with aqueous MeOH and NaHCO3 solution
  3. extractionextracted with EtOAc
  4. customThe combined organic extracts were evaporated
  5. customthe residue was purified by flash column chromatography on silica gel (0-100% gradient CH2Cl2/EtOAc, followed by 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-63dfd6c182984543a39abdf6012c7516
Source dataset
uspto-grants-2013_03
Patent number
US08399681B2

Reaction notes

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