Boron tribromide → HCID 86584911, compound

HRID 2250696Notes

Reaction equation

HRID 2250696 reaction equation
C[O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13]([C:15]3[S:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[O:14])[S:11][C:7]=2[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(OCC)(=O)C>[OH:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13]([C:15]3[S:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[O:14])[S:11][C:7]=2[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10199799HCID 10199799, compound

Product 1

HCID 86584911HCID 86584911, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-methyl-thiophene-2-carboxylic acid (4-methoxy-7-phenyl-benzothiazol-2-yl)-amide (630 mg, 1.7 mmol) is slowly trated with boron tribromide (16 ml, 1.0 M in dichloromethane) at 0° C. The reaction is slowly warmed to ambient temperature and stirred for further 72 h. The mixture is diluted with ethyl acetate and extracted twice with water and once with brine. After drying over sodium sulfate, the solvent is removed in vacuo. Flash chromatography (silica, eluent ethyl acetate/hexane 1:1) and final recrystallization from tetrahydrofurane/hexane yields 118 mg (19%) of the product as white solid. MS: m/e=367 (M+H+).

Workup

  1. extractionextracted twice with water and once with brine
  2. dry with materialAfter drying over sodium sulfate
  3. customthe solvent is removed in vacuo
  4. customFlash chromatography (silica, eluent ethyl acetate/hexane 1:1) and final recrystallization from tetrahydrofurane/hexane

Sources & evidence

ORD record
ord-a44f076b39b34c31b5a42401941ccd03
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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