Cesium carbonate → HCID 59053719, compound

HRID 875049Notes

Reaction equation

HRID 875049 reaction equation
C1(S([N:10]2[C:14]3=[CH:15][N:16]=[CH:17][CH:18]=[C:13]3[C:12]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([C:28]5[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=5)[CH:26]=4)[NH:21][CH:20]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(O)C(F)(F)F.C1COCC1>[CH3:33][N:31]1[CH:32]=[C:28]([C:25]2[CH:26]=[C:27]3[C:19]([C:12]4[C:13]5[C:14](=[CH:15][N:16]=[CH:17][CH:18]=5)[NH:10][CH:11]=4)=[CH:20][NH:21][C:22]3=[N:23][CH:24]=2)[CH:29]=[N:30]1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 59053713HCID 59053713, compound

Product 1

HCID 59053719HCID 59053719, compound

Reagents, catalysts & solvents 2

HCID 64092,2,2-TrifluoroethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 112 mg (0.25 mmol) of 1-benzenesulfonyl-3-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrolo[2,3-c]pyridine (“A14”) and 261 mg (0.74 mmol) of caesium carbonate in 1 ml of trifluoroethanol and 2 ml of THF is stirred at 65° C. for 18 hours. The reaction mixture is evaporated, and the residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent: 3-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-1H-pyrrolo[2,3-c]pyridine as colourless solid.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-eec32430390b4ef29a9711141f81325e
Source dataset
uspto-grants-2015_03
Patent number
US08981101B2

Reaction notes

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