Bis(tributyltin) oxide → 4-(2-Fluoro-4-iodo-phenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid

HRID 79017Notes

Reaction equation

HRID 79017 reaction equation
C[O:2][C:3]([C:5]1[C:6]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=2[F:32])=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[N:9]=[CH:8]2)=[O:4].CCCC[Sn](O[Sn](CCCC)(CCCC)CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[F:32][C:26]1[CH:27]=[C:28]([I:31])[CH:29]=[CH:30][C:25]=1[NH:24][C:6]1[C:5]([C:3]([OH:4])=[O:2])=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[N:9][N:10]2[S:14]([C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 16682746Bis(tributyltin) oxideHCID 670840904-(2-Fluoro-4-iodophenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid methyl ester

Product 1

HCID 670840434-(2-Fluoro-4-iodo-phenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(2-fluoro-4-iodophenylamino)-1-(toluene-4-sulfonyl)-1H-indazole-5-carboxylic acid methyl ester (0.51 g, 0.91 mmol) in toluene (5 mL) was added bis(tributyltin) oxide (0.92 mL, 1.8 mmol) and the reaction mixture heated at reflux for 48 hours. The reaction mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (Si—PPC, gradient 0-10% methanol in DCM) to yield the title compound as a light brown solid (0.46 g, 92%). LCMS (Method B): RT=4.27 min, [M+H]+=552.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 48 hours
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f7316022bc6d476a9d325f95253c47c7
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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