Boron tribromide → HCID 67240265, compound

HRID 2384626Notes

Reaction equation

HRID 2384626 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-a4f8f3b555fa404bb1e9498a64853828
Source dataset
uspto-grants-2012_09
Patent number
US08263781B2

Reaction notes

Loading…