Allyl bromide → HCID 178513839, compound

HRID 457341Notes

Reaction equation

HRID 457341 reaction equation
C(NS(C1C=CC([N:14]2[C:22]3[C:21]4[CH:23]=[C:24]([NH:27][C:28](=[O:36])[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[Cl:35])[CH:25]=[CH:26][C:20]=4[CH2:19][CH2:18][C:17]=3[C:16]([C:37]([NH2:39])=[O:38])=[N:15]2)=CC=1)(=O)=O)(=O)C.C(Br)C=C>CN(C=O)C>[Cl:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:28]([NH:27][C:24]1[CH:25]=[CH:26][C:20]2[CH2:19][CH2:18][C:17]3[C:16]([C:37]([NH2:39])=[O:38])=[N:15][NH:14][C:22]=3[C:21]=2[CH:23]=1)=[O:36]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 22291714HCID 22291714, compound

Product 1

HCID 178513839HCID 178513839, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of the Cs+ salt of 1-{4-[(acetylamino)sulfonyl]phenyl}-8-[(2-chlorobenzoyl)amino]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (637 mg, 0.92 mmol) in DMF (8 mL) was added a solution of allyl bromide (111 mg, 0.92 mmol). The solution was stirred at room temperature for over the weekend and concentrated. To the mixture was added MeOH—H2O (2:1). A precipitate was formed. It was filtered to give a yellow solid of 1-(4-[acetyl(allyl)amino]sulfonyl}phenyl)-8-[(2-chlorobenzoyl)amino]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (360 mg, 65%.)

Workup

  1. concentrationconcentrated
  2. additionTo the mixture was added MeOH—H2O (2:1)
  3. customA precipitate was formed
  4. filtrationIt was filtered

Sources & evidence

ORD record
ord-bc67c705bceb42ec83775c5064742842
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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