8-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-ethynylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide → 8-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-vinylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

HRID 457335

Reaction equation

HRID 457335 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:34]=[CH:33][C:14]3[CH2:15][CH2:16][C:17]4[C:18]([C:30]([NH2:32])=[O:31])=[N:19][N:20]([C:22]5[CH:27]=[CH:26][C:25]([C:28]#[CH:29])=[CH:24][CH:23]=5)[C:21]=4[C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1>CN(C=O)C.CS(C)=O>[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:34]=[CH:33][C:14]3[CH2:15][CH2:16][C:17]4[C:18]([C:30]([NH2:32])=[O:31])=[N:19][N:20]([C:22]5[CH:27]=[CH:26][C:25]([CH:28]=[CH2:29])=[CH:24][CH:23]=5)[C:21]=4[C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 222915468-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-ethynylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

Product 1

HCID 222916928-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-vinylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamideYield 47%

Reagents, catalysts & solvents 1

HCID 3013483N,N-dimethylformamide; methylsulfinylmethaneSolvent

Procedure

A solution of 8-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-ethynylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (557 mg, 1.19 mmol) in DMF-DMSO (20 mL-1 mL) was treated at RT with H2 (5 psi) and Pd—CaSO4 (5%, 100 mg) for 12 min. The mixture was filtered through celite pad, concentrated and added water. The solid product was collected via filtration, washed with water and ether, and dried to give product (262 mg, 47%). 1H NMR was consistent with its structure.

Workup

  1. filtrationThe mixture was filtered through celite pad
  2. concentrationconcentrated
  3. additionadded water
  4. filtrationThe solid product was collected via filtration
  5. washwashed with water and ether
  6. customdried

Sources & evidence

ORD record
ord-a8d45760e38e424fbd2163fe3a51c169
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Linked notes

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