Pyridine → HCID 57428078, compound

HRID 270331Notes

Reaction equation

HRID 270331 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[C:18][CH2:19][CH2:20][OH:21])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].N1C=CC=CC=1.OS([O-])(=O)=O.[K+]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[C:18][CH2:19][CH2:20][O:21][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516920Potassium bisulfateHCID 223139024-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-yn-1-ol

Product 1

HCID 57428078HCID 57428078, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

365 mg (1.02 mmol) 4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-yn-1-ol in 7 ml CH2Cl2 were treated with 94 μl (1.21 mmol) methane sulfonic acid chloride, 0.13 ml (1.53 mmol) pyridine and 135 mg (1.2 mmol) DMAP at 0° C. The solution was stirred at RT over night, was diluted with water and acidified with 10% aq. KHSO4. The inorganic phase was extracted with CH2Cl2. The combined organic phases were washed with NaHCO3 solution, brine and dried over Na2SO4. Evaporation gave 446 mg crude Methanesulfonic acid 4-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yl]-but-3-ynyl ester, MS: 436 (MH+).

Workup

  1. extractionThe inorganic phase was extracted with CH2Cl2
  2. washThe combined organic phases were washed with NaHCO3 solution, brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation

Sources & evidence

ORD record
ord-43812b33ece84242b0fc6493716cb2c7
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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