Boron tribromide → 2-Hydroxy-N-[3-hydroxy-4-(6-hydroxy-1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethoxy)benzamide

HRID 339539Notes

Reaction equation

HRID 339539 reaction equation
C[O:2][C:3]1[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][C:4]=1[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([O:23]C)[CH:20]=[CH:19][C:17]=3[N:18]=2)=[C:10]([O:25]C)[CH:9]=1)=[O:6].B(Br)(Br)Br.CCCCCC.CCOC(C)=O.CO>C(Cl)Cl>[OH:2][C:3]1[CH:30]=[CH:29][C:28]([O:31][C:32]([F:34])([F:35])[F:33])=[CH:27][C:4]=1[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:17]=3[N:18]=2)=[C:10]([OH:25])[CH:9]=1)=[O:6]

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 21879739Ethyl acetate hexane methanolHCID 673117622-methoxy-N-[3-methoxy-4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethoxy)benzamide

Product 1

HCID 1360605302-Hydroxy-N-[3-hydroxy-4-(6-hydroxy-1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethoxy)benzamideYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared as described in the Demethylation section using 2-methoxy-N-[3-methoxy-4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethoxy)benzamide (0.30 g, 0.595 mmol) in dry DCM (12 ml) and BBr3 (1.0M in DCM, 1.9 ml, 1.9 mmol) at −78° C. under an atmosphere of argon. Additional BBr3 (1.0 M in DCM, 1.9 ml, 1.9 mmol) was added dropwise and the reaction mixture stirred at room temperature for 4 d to give the title compound (88 mg, 32%) as a pale yellow solid after work-up and flash chromatography (4:2:0.3 Hexane/EtOAc/MeOH).

Workup

  1. customPrepared
  2. customat −78° C.

Sources & evidence

ORD record
ord-29dec820e11744c6b218d5b1ffd26680
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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