Water → HCID 11305553, compound

HRID 2243147Notes

Reaction equation

HRID 2243147 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][CH:11]([C:17]2[N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=3)[CH:19]=[CH:20][N:21]=2)[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])(=[O:9])=[O:8])=[CH:4][CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][CH:11]([C:17]2[N:18]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)[CH:19]=[CH:20][N:21]=2)[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])(=[O:8])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 11385812HCID 11385812, compound

Product 1

HCID 11305553HCID 11305553, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-chloro-N-{2-ethyl-1-[1-(4-methoxybenzyl)-1H-imidazol-2-yl]butyl}thiophene-2-sulfonamide (250 mg, 0.534 mmol) in CH2Cl2 (5 mL) at −78° C. was added a solution of boron tribromide (1M in CH2Cl2, 0.80 mL, 0.80 mmol) dropwise. After 4 h, the reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was then slowly poured into H2O, extracted 3 times with CH2Cl2, dried over MgSO4, filtered and concentrated in vacuo. The material was purified by column chromatography (SiO2, CHCl3, then 2% MeOH/CHCl3) to yield a clear oil in 58% yield.

Workup

  1. extractionextracted 3 times with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe material was purified by column chromatography (SiO2, CHCl3
  6. custom2% MeOH/CHCl3) to yield a clear oil in 58% yield

Sources & evidence

ORD record
ord-f95a89dbb524494fb75c795d0ac56321
Source dataset
uspto-grants-2010_03
Patent number
US07674813B2

Reaction notes

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