5-Bromo-2-methoxybenzene-1-sulfonyl chloride → HCID 57473902, compound

HRID 1868408Notes

Reaction equation

HRID 1868408 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]([NH2:14])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[Br:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([S:24](Cl)(=[O:26])=[O:25])[CH:23]=1>N1C=CC=CC=1.C(O)(=O)C.C(OCC)(=O)C>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([S:24]([NH:14][CH:3]([CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)[C:2]([F:1])([F:15])[F:16])(=[O:25])=[O:26])[CH:23]=1

Participants

6

Reactant 2

HCID 5200205-Bromo-2-methoxybenzene-1-sulfonyl chlorideHCID 539884361,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-amine

Product 1

HCID 57473902HCID 57473902, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 100 mg (0.44 mmol) of 2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethylamine and 143 mg (0.50 mmol) of 5-bromo-2-methoxybenzenesulfonyl chloride in 4 mL of pyridine was warmed at 65° C. After 16 hours, the mixture was cooled and concentrated to afford a thick oily residue. The residue was diluted with 10% acetic acid and extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, decanted, and concentrated in vacuo. The crude material was purified by preparative TLC using ethyl acetate-hexanes (15:85). Material from the plate was isolated by suspending the silica gel in ethyl acetate followed by filtration. The filtrate was concentrated in vacuo to afford 66 mg (32%) of the title compound as a crystalline solid.

Workup

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated
  3. customto afford a thick oily residue
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. customdecanted
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by preparative TLC
  10. customMaterial from the plate was isolated
  11. filtrationfollowed by filtration
  12. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-011b92e0a15f42ecb0ea97c682b9fc53
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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