Sodium Bicarbonate → 2-Methyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

HRID 1695735Notes

Reaction equation

HRID 1695735 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7](Cl)=[O:8])[N:6]=1.[C:10]1([S:16]([N:19]2[C:27]3[CH:26]=[C:25]([Sn:28]([CH3:31])([CH3:30])[CH3:29])[CH:24]=[C:23]([NH2:32])[C:22]=3[CH:21]=[N:20]2)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:32][C:23]2[CH:24]=[C:25]([Sn:28]([CH3:31])([CH3:30])[CH3:29])[CH:26]=[C:27]3[C:22]=2[CH:21]=[N:20][N:19]3[S:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:18])=[O:17])=[O:8])[N:6]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 211839592-Methyl-1,3-thiazole-4-carbonyl chlorideHCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine

Product 1

HCID 582558202-Methyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamideYield 96.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Procedure

2-Methyl-1,3-thiazole-4-carbonyl chloride (350 mg) in DCM (4 ml) was added dropwise to 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (300 mg) in DCM (15 ml) and pyridine (0.167 ml). The reaction was stirred at room temperature overnight. Saturated sodium bicarbonate (aq) (25 ml) was added and the reaction vigorously stirred for 15 min. The DCM was passed through a hydrophobic frit then evaporated to dryness. The residue was dissolved in DCM and purified on a silica cartridge, preconditioned with cyclohexane, washing with cyclohexane followed by elution with ether. The ether was evaporated to give title compound (373 mg).

Workup

  1. customthe reaction
  2. stirringvigorously stirred for 15 min
  3. customthen evaporated to dryness
  4. dissolutionThe residue was dissolved in DCM
  5. custompurified on a silica cartridge
  6. washwashing with cyclohexane
  7. washfollowed by elution with ether
  8. customThe ether was evaporated

Sources & evidence

ORD record
ord-cab2dbf892a047a2b0bd3b7f01e7983a
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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