Cesium carbonate → HCID 118415302, compound

HRID 1051408Notes

Reaction equation

HRID 1051408 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[F:18])[NH:14][N:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[I:33]>CN1C(=O)CCC1>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[F:18])[N:14]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[I:33])[N:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 114264722-Iodobenzyl BromideHCID 90111076HCID 90111076, compound

Product 1

HCID 118415302HCID 118415302, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 5-(benzylthio)-6-fluoro-1H-indazole (1-2, 1.5 g, 5.81 mmol, 1.0 equiv) in NMP (29.0 mL) was added cesium carbonate (5.68 g, 17.42 mmol, 3.0 equiv) and 1-(bromomethyl)-2-iodobenzene (2.59 g, 8.71 mmol, 1.5 equiv) and the reaction mixture was stirred at ambient temperature. Upon completion, the reaction mixture was washed with water and extracted with EtOAc. The organic phase was dried over Na2SO4, filtered and concentrated and the residue was purified by normal phase chromatography followed by reverse phase chromatography (50%→100% 0.1% TFA in ACN: 0.1% TFA in water) to yield the desired regioisomer. ESI+ MS [M+H]+ C21H16FIN2S: 475.1 found, 475.3 required.

Workup

  1. washUpon completion, the reaction mixture was washed with water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by normal phase chromatography
  7. customto yield the desired regioisomer

Sources & evidence

ORD record
ord-e58e17cd188b4793af218b0f57a5cd84
Source dataset
uspto-grants-2016_07
Patent number
US09388179B2

Reaction notes

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