Cesium carbonate → HCID 24794475, compound

HRID 1875453Notes

Reaction equation

HRID 1875453 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1.Cl[C:19]1[N:24]=[C:23]([NH2:25])[N:22]=[C:21]([NH2:26])[N:20]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:19]2[N:24]=[C:23]([NH2:25])[N:22]=[C:21]([NH2:26])[N:20]=2)[N:6]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 188311,3,5-Triazine-2,4-diamine, 6-chloro-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178505621HCID 178505621, compound

Product 1

HCID 24794475HCID 24794475, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 150 mg (0.66 mmol) of 3-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine from example 12A, 96 mg (0.66 mmol) of 6-chloro-1,3,5-triazine-2,4-diamine, 12 mg (0.013 mmol) of tris(di-benzylideneacetone)dipalladium, 19 mg (0.040 mmol) of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPHOS) and 300 mg (0.92 mmol) of cesium carbonate in 4 ml of degassed toluene is heated at 90° C. for 20 h. It is then diluted with water and a little methanol and extracted with ethyl acetate. The organic phase is concentrated in vacuo, and the residue is stirred with methanol and filtered off with suction. 62 mg (28% of theory) of the desired compound are obtained as beige-colored crystals in this way.

Workup

  1. extractiona little methanol and extracted with ethyl acetate
  2. concentrationThe organic phase is concentrated in vacuo
  3. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-a2b432e7c43845f486404544dca2c327
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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