Potassium Phosphate, Tribasic → CD-160130

HRID 1182848Notes

Reaction equation

HRID 1182848 reaction equation
Br[C:2]1[CH:3]=[CH:4][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:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:22]([O:21][C:11]1[C:7]2[NH:8][C:9]3[CH:10]=[C:2]([C:32]4[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=4)[CH:3]=[CH:4][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 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66863934HCID 66863934, compound

Product 1

HCID 24990553CD-160130

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

150 mg (0.4 mmol) 7-bromo-4-ethoxy-2-(piperazin-1-yl)-5H-pyrimido[5,4-b]indole (Example 4), 123 mg (0.6 mmol) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 276 mg (1.2 mmol) K3PO4×H2O, 6.6 mg (16 mmol) S-Phos and 9.2 mg (8 mmol) Pd(PPh3)4 in 6 ml THF were heated in a microwave oven to 120° C. for 2 h. Then, the solvent was removed and following LC (CH2Cl2/MeOH, O-20%) 93 mg (62%) of the title substance was obtained ESI-MS [m/z]: 375 [M+H]+

Workup

  1. customThen, the solvent was removed
  2. customO-20%) 93 mg (62%) of the title substance was obtained ESI-MS [m/z]

Sources & evidence

ORD record
ord-6ab0826f7835467ab3b76b3f1bf9d36d
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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