Water → HCID 11362679, compound

HRID 748050Notes

Reaction equation

HRID 748050 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 −780C 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 x'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 x'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-fff4b8af5904499db4553c33defdc403
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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