Potassium Carbonate → HCID 24990556, compound

HRID 1182834Notes

Reaction equation

HRID 1182834 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:39]=[CH:38][N:37]=[CH:36][CH:35]=2)O1.C([O-])([O-])=O.[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:22]([O:21][C:11]1[C:7]2[NH:8][C:9]3[CH:10]=[C:2]([C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)[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

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66863771HCID 66863771, compound

Product 1

HCID 24990556HCID 24990556, compound

Reagents, catalysts & solvents 2

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

Procedure

60 mg (0.15 mmol) 7-bromo-4-ethoxy-9-methoxy-2-(piperazin-1-yl)-5H-pyrimido[5,4-b]indole (Example 1), 47 mg (0.23 mmol) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 61 mg (0.45 mmol) K2CO3, 2.4 mg (6.0 μmol) S-Phos and 0.7 mg (3.0 μmol) Pd(OAc)2 in 6 ml dioxan were heated in a microwave oven to 120° C. for 1 h. Thereafter, the solvent was removed and following LC (CH2Cl2:MeOH, 0-30%) 27 mg (45%) of the title substance was obtained. ESI-MS [m/z]: 405 [M+H]+

Workup

  1. customThereafter, the solvent was removed
  2. customwas obtained

Sources & evidence

ORD record
ord-c3baba9e516949d19b2f91842eab3ec1
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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