Pyridine → 1,4-Dimethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-3-carboxamide

HRID 520577Notes

Reaction equation

HRID 520577 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[C:16]([Sn:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=[C:14]([NH2:23])[C:13]=3[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH3:30][N:31]1[CH:35]=[C:34]([CH3:36])[C:33]([C:37](Cl)=[O:38])=[N:32]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:30][N:31]1[CH:35]=[C:34]([CH3:36])[C:33]([C:37]([NH:23][C:14]2[CH:15]=[C:16]([Sn:19]([CH3:20])([CH3:22])[CH3:21])[CH:17]=[C:18]3[C:13]=2[CH:12]=[N:11][N:10]3[S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])=[O:38])=[N:32]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amineHCID 583563801,4-Dimethyl-1H-pyrazole-3-carbonyl chloride

Product 1

HCID 583564471,4-Dimethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1-(Phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (250 mg) was dissolved in DCM (10 ml) and pyridine (0.051 ml) was added. 1,4-Dimethyl-1H-pyrazole-3-carbonyl chloride (100 mg) in DCM (5 ml) was added dropwise. The reaction was stirred at RT for 2 h. After this time saturated sodium bicarbonate aq (25 ml) was added and the reaction was stirred vigorously for 5 min before the DCM was passed through a hydrophobic frit then evaporated to dryness. The residue was dissolved in DCM, and then applied to the top of a 20 g silica cartridge preconditioned with cyclohexane. The column was washed with 50% cyclohexane:ether (100 ml), before the compound was eluted with ether, then 5% methanol in ether. The product containing fractions were evaporated to dryness to afford the title compound, 310 mg.

Workup

  1. customthen evaporated to dryness
  2. dissolutionThe residue was dissolved in DCM
  3. washThe column was washed with 50% cyclohexane
  4. washether (100 ml), before the compound was eluted with ether
  5. additionThe product containing fractions
  6. customwere evaporated to dryness

Sources & evidence

ORD record
ord-ae9910811cc14d4d961cf04a03b6d0bc
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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