Potassium Phosphate, Tribasic → HCID 24853524, compound

HRID 1182833Notes

Reaction equation

HRID 1182833 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:24][CH3:25])[C:5]2[C:6]3[N:14]=[C:13]([N:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[N:12]=[C:11]([O:21][CH2:22][CH3:23])[C:7]=3[NH:8][C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[NH2:36])O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH2:22]([O:21][C:11]1[C:7]2[NH:8][C:9]3[CH:10]=[C:2]([C:34]4[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=4[NH2:36])[CH:3]=[C:4]([O:24][CH3:25])[C:5]=3[C:6]=2[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:12]=1)[CH3:23]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66863771HCID 66863771, compound

Product 1

HCID 24853524HCID 24853524, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

70 mg (0.17 mmol) 7-bromo-4-ethoxy-9-methoxy-2-(piperazin-1-yl)-5H-pyrimido[5,4-b]indole, 56 mg (0.26 mmol) 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 119 mg (0.51 mmol) K3PO4×H2O, 2.8 mg (6.8 μmol) S-Phos and 0.8 mg (3.4 μmol) Pd(OAc)2 in 6 ml dioxan were heated in a microwave oven to 120° C. for 1 h. Then, the solvent was removed and after LC (CH2Cl2:MeOH, 0-20%) 20 mg (24%) of the title substance was obtained. ESI-MS [m/z]: 419 [M+H]+

Workup

  1. customThen, the solvent was removed
  2. customafter LC (CH2Cl2:MeOH, 0-20%) 20 mg (24%) of the title substance was obtained

Sources & evidence

ORD record
ord-81b40bd668fa4b9aa18cf13d0fec6464
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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