Benzenesulfonyl chloride → HCID 67513798, compound

HRID 1182919Notes

Reaction equation

HRID 1182919 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[CH:9]=2)[NH:4][CH:3]=1.C(N(CC)CC)C.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:24]1([S:30]([N:4]2[C:5]3=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=4)[CH:9]=[C:10]3[C:2]([I:1])=[CH:3]2)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 66778502HCID 66778502, compound

Product 1

HCID 67513798HCID 67513798, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The 3-iodo-5-(1-methylpyrazol-4-yl)-7-azaindole prepared in accordance with WO 2008155000 (34 g) is suspended in 350 ml of dichloromethane, and 43.5 ml of triethylamine and 2.6 g of 4-(dimethylamino)pyridine are added. 17.5 ml of benzenesulfonyl chloride which has previously been diluted with 150 of dichloromethane are added to this mixture. After 2 h, the reaction is complete. The organic phase is extracted three times with water, and the organic phase is dried over sodium sulfate. After removal of the solvent, the residue is taken up in ethyl acetate, the precipitate is filtered off, rinsed with ethyl acetate, and the product is dried in air to give 44 g (90%) of beige crystals; (Rt: 2.467 min; M+H+: 464.9).

Workup

  1. additionare added to this mixture
  2. extractionThe organic phase is extracted three times with water
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. customAfter removal of the solvent
  5. filtrationthe precipitate is filtered off
  6. washrinsed with ethyl acetate
  7. customthe product is dried in air

Sources & evidence

ORD record
ord-1ccd26c9e7254e7797c5cd24031af76c
Source dataset
uspto-grants-2014_03
Patent number
US08664236B2

Reaction notes

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