Diisopropylethylamine → 2-Fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzene-1-sulfonyl chloride

HRID 628145Notes

Reaction equation

HRID 628145 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].CCN(C(C)C)C(C)C.[Cl:14][S:15]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[F:27])[C:21](Cl)=[O:22])(=[O:17])=[O:16]>C(Cl)Cl>[F:27][C:26]1[CH:25]=[CH:24][C:20]([C:21](=[O:22])[NH:4][CH2:1][C:2]#[CH:3])=[CH:19][C:18]=1[S:15]([Cl:14])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 239041PropargylamineHCID 581074393-(Chlorosulfonyl)-4-fluorobenzoyl chloride

Product 1

HCID 867153592-Fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzene-1-sulfonyl chlorideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Propargylamine (0.67 mL, 10.5 mmol) and DIEA (1.83 mL, 10.5 mmol) in DCM (10 mL) were added dropwise to 3-(chlorosulfonyl)-4-fluorobenzoyl chloride (2) in DCM (10 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 15 minutes. The reaction was washed with 2N HCl and brine, dried (MgSO4) and evaporated. The residue was purified by Biotage flash column chromatography (30% EtOAc/Hep) to give product as an oil (2.52 g, 87%).

Workup

  1. washThe reaction was washed with 2N HCl and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by Biotage flash column chromatography (30% EtOAc/Hep)

Sources & evidence

ORD record
ord-0e6b78a822574245b30ec170f47836b8
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

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