Potassium Phosphate, Tribasic → 1-{[(1R,2R,4R)-4-Hydroxy-2-methylcyclohexyl]amino}-7-(1-methyl-1H-pyrazol-4-yl)-5H-pyrido[4,3-b]indole-4-carbonitrile

HRID 1971010Notes

Reaction equation

HRID 1971010 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([NH:15][C@@H:16]4[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18][C@H:17]4[CH3:23])=[N:13][CH:12]=[C:11]([C:24]#[N:25])[C:7]=3[NH:8][C:9]=2[CH:10]=1.[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:22][C@@H:19]1[CH2:20][CH2:21][C@@H:16]([NH:15][C:14]2[C:6]3[C:5]4[CH:4]=[CH:3][C:2]([C:30]5[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=5)=[CH:10][C:9]=4[NH:8][C:7]=3[C:11]([C:24]#[N:25])=[CH:12][N:13]=2)[C@H:17]([CH3:23])[CH2:18]1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 686692267-Chloro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

Product 1

HCID 686700021-{[(1R,2R,4R)-4-Hydroxy-2-methylcyclohexyl]amino}-7-(1-methyl-1H-pyrazol-4-yl)-5H-pyrido[4,3-b]indole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A flask containing 7-chloro-1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (37 mg, 0.104 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (65 mg, 0.31 mmol), Pd2(dba)3 (9.6 mg, 0.010 mmol), tricyclohexylphosphine (7.3 mg, 0.026 mmol), and K3PO4 (1.27 M, 0.28 mL, 0.35 mmol) was evacuated and refilled with nitrogen (×3). Dioxane (3 mL) was added to the mixture, and the resultant reaction mixture was heated to 100° C. overnight, and purified by flash chromatography to afford the title compound. LRMS (APCI) calc'd for (C23H24N6O) [M+H]+, 401.2. found 401.1.

Workup

  1. customwas evacuated
  2. additionrefilled with nitrogen (×3)
  3. additionDioxane (3 mL) was added to the mixture
  4. customthe resultant reaction mixture
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7e83b86f01d144778b0cba3801ebfaf8
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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