Potassium Phosphate, Tribasic → HCID 86271598, compound

HRID 1466213Notes

Reaction equation

HRID 1466213 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:17]=[C:18]2[C:33]([CH3:34])=[N:32][N:31]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:19]2=[N:20][C:21]=1[N:22]([CH2:27][CH:28]1[CH2:30][CH2:29]1)[CH2:23][CH:24]1[CH2:26][CH2:25]1)[C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][N:9]=1.[CH:48]1(B(O)O)[CH2:50][CH2:49]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:17]=[C:18]2[C:33]([CH3:34])=[N:32][N:31]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:19]2=[N:20][C:21]=1[N:22]([CH2:27][CH:28]1[CH2:30][CH2:29]1)[CH2:23][CH:24]1[CH2:26][CH2:25]1)[C:8]1[CH:13]=[CH:12][C:11]([CH:48]2[CH2:50][CH2:49]2)=[CH:10][N:9]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 89480386HCID 89480386, compound

Product 1

HCID 86271598HCID 86271598, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

5-(((3,5-bis(trifluoromethyl)benzyl)(5-bromopyridin-2-yl)amino)methyl)-1-(tert-butyl)-N,N-bis(cyclopropylmethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-amine (0.05 g, 0.069 mmol) as prepared above, cyclopropyl boronic acid (0.007 g, 0.083 mmol) were dissolved in toluene (10 ml). To this tricyclohexylphosphine (0.002 g, 0.0069 mmol), Pd(OAc)2 (0.0007 g, 0.0034 mmol), K3PO4 (0.051 g, 0.241 mmol) were added. The mixture was stirred at 100° C. for 16 hr. The reaction mixture was diluted with water, extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product thus obtained, was purified by column chromatography using silica gel 60-120 mesh, 10% EtOAc in petroleum ether as the eluent to obtain the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product thus obtained
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6382162085684776ad46e81118b21146
Source dataset
uspto-grants-2015_04
Patent number
US09000007B2

Reaction notes

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