Benzenesulfonyl chloride, 3,4-dichloro- → HCID 67218945, compound

HRID 1254862Notes

Reaction equation

HRID 1254862 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[Cl:14])[NH:7][C:6]=1[CH3:15].CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[Cl:35][C:36]1[CH:37]=[C:38]([S:43](Cl)(=[O:45])=[O:44])[CH:39]=[CH:40][C:41]=1[Cl:42]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[Cl:14])[N:7]([S:43]([C:38]2[CH:39]=[CH:40][C:41]([Cl:42])=[C:36]([Cl:35])[CH:37]=2)(=[O:45])=[O:44])[C:6]=1[CH3:15]

Participants

5

Reactant 3

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 67219047HCID 67219047, compound

Product 1

HCID 67218945HCID 67218945, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (58 mg, 0.24 mmol) in DMF (1.2 mL) is added BEMP (113 μL, 0.39 mmol). The reaction mixture is stirred at ambient temperature for 40 minutes. 3,4-Dichloro-benzenesulfonyl chloride (60 μL, 0.39 mmol) is added and the reaction mixture is stirred for 10 minutes at ambient temperature. The reaction mixture is poured into ice cold water, extracted with EtOAc, washed with brine, dried (Na2SO4) and evaporated. The crude product is purified by column chromatography on silica gel using 1:8 EtOAc/iso-hexane as the eluent, furnishing [4-chloro-1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-yl]-acetic acid methyl ester; MH+=449.

Workup

  1. stirringthe reaction mixture is stirred for 10 minutes at ambient temperature
  2. additionThe reaction mixture is poured into ice cold water
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude product is purified by column chromatography on silica gel using 1:8 EtOAc/iso-hexane as the eluent

Sources & evidence

ORD record
ord-25ae2eab103a416c87d383682816cbab
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

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