Boron tribromide → HCID 58342068, compound

HRID 339538Notes

Reaction equation

HRID 339538 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:16][C:17]4[CH:23]=[C:22]([O:24]C)[CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].B(Br)(Br)Br.C(Cl)Cl.CCOC(C)=O>C(Cl)Cl>[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[S:16][C:17]4[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:13][CH:14]=2)=[O:7])=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 21226138Dichloromethane ethylacetateHCID 67312218HCID 67312218, compound

Product 1

HCID 58342068HCID 58342068, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared as described in the Demethylation section using 4-amino-3-trifluoromethyl-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide (0.30 g, 0.68 mmol) in dry DCM (10 ml) and BBr3 (1.0 M solution in DCM, 5.42 ml, 5.42 mmol) to give the title compound (0.064 g, 22%) as an orange solid after work-up and flash chromatography (3:1 DCM/EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6af0af237904426ea1c9e181ea22ab45
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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