Cesium carbonate → HCID 73438552, compound

HRID 1049387Notes

Reaction equation

HRID 1049387 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([C:19]3[C:28]4[C:23](=[CH:24][N:25]=[CH:26][CH:27]=4)[C:22]([NH2:29])=[N:21][CH:20]=3)=[C:11]2[CH3:30])(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.C(O)C(F)(F)F>[CH3:30][C:11]1[NH:10][C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]=1[C:19]1[C:28]2[C:23](=[CH:24][N:25]=[CH:26][CH:27]=2)[C:22]([NH2:29])=[N:21][CH:20]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 90092396HCID 90092396, compound

Product 1

HCID 73438552HCID 73438552, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 66819073HCID 66819073, compoundSolvent

Procedure

A mixture of 23 g of 4-(1-benzenesulfonyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,7-naphthyridin-1-ylamine and 26 g of caesium carbonate in 400 ml of THF/trifluoroethanol (1:1 vol) is heated under reflux for 20 h. The mixture is cooled, the solvent is removed, and the product is purified by means of flash chromatography over 220 g of silica with a methanol gradient in ethyl acetate with 150 ml/min with UV detection at 254 nm, giving 12.2 g of 4-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,7-naphthyridin-1-ylamine, M˜275.31, M+H found 276.2;

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 20 h
  3. temperatureThe mixture is cooled
  4. customthe solvent is removed
  5. customthe product is purified by means of flash chromatography over 220 g of silica with a methanol gradient in ethyl acetate with 150 ml/min with UV detection at 254 nm

Sources & evidence

ORD record
ord-6d08544a6a9642d788767797e956385a
Source dataset
uspto-grants-2016_07
Patent number
US09382244B2

Reaction notes

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