Water → HCID 11362679, compound

HRID 2243131Notes

Reaction equation

HRID 2243131 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][CH:11]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=3)[N:20]=[CH:19][CH:18]=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:21]([C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)[N:20]=[CH:19][CH:18]=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 tribromide2×HCID 11476543HCID 11476543, compound

Product 1

HCID 11362679HCID 11362679, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-chloro-N-{2-ethyl-1-[1-(4-methoxyphenyl)-1H-pyrazol-5-yl]butyl}thiophene-2-sulfonamide (0.30 g, 0.66 mmol) in CH2Cl2 (10 mL) at −78° C. was added a solution of boron tribromide (1.0 M, 0.99 mL, 0.99 mmol) dropwise. After 4 h at −78° C. and 18 h at room temperature, another 1.5 eq BBr3 (0.99 mL) was added at −78° C. The reaction mixture was gradually warmed to room temperature and stirred for 18 h. The reaction mixture was slowly poured into H2O and extracted with CH2Cl2 (3×'s), dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude solid was purified by column chromatography (SiO2, EtOAc/hexane, 2:3), then precipitated with Et2O/hexane to yield a white solid in 34% yield.

Workup

  1. extractionextracted with CH2Cl2 (3×'s),
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude solid was purified by column chromatography (SiO2, EtOAc/hexane, 2:3)
  6. customprecipitated with Et2O/hexane
  7. customto yield a white solid in 34% yield

Sources & evidence

ORD record
ord-6f87f07b240a48f4887325639d4084db
Source dataset
uspto-grants-2010_03
Patent number
US07674813B2

Reaction notes

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