Potassium Phosphate, Tribasic → HCID 66604014, compound

HRID 2410850Notes

Reaction equation

HRID 2410850 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([O:17][C:18]1[C:19]2[C:20]3[N:30]=[C:29](Br)[CH:28]=[C:27]([C:32]([O:34][CH3:35])=[O:33])[C:21]=3[NH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:10]([O:17][C:18]1[C:19]2[C:20]3[N:30]=[C:29]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:28]=[C:27]([C:32]([O:34][CH3:35])=[O:33])[C:21]=3[NH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86663063HCID 86663063, compound

Product 1

HCID 66604014HCID 66604014, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
80 °C

Procedure

A flask containing a mixture of phenylboronic acid (0.889 g, 7.29 mmol), methyl 9-(benzyloxy)-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (1.50 g, 3.65 mmol), powdered potassium phosphate tribasic (2.48 g, 11 7 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (0.348 g, 0.729 mmol), and Pd(OAc)2 (0.082 g, 0.365 mmol) was flushed with nitrogen. THF (12 mL) was added and the mixture was heated at 80° C. for 2 hr. The reaction was diluted with EtOAc, washed with water, sat. aq. Na2CO3 solution, brine, and dried with sodium sulfate. The solvent was removed and the residue was suspended in a little EtOAc. Filtration and washing with EtOAc, afforded methyl 9-(benzyloxy)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (1.47 g, 3.42 mmol, 94%). MS (ESI) m/z 408.9 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.68 (1H, s), 8.33 (1H, s), 8.28 (2H, d, J=7.32 Hz), 7.87 (2H, d J=7.63 Hz), 7.37-7.57 (8H, m), 6.99 (1H, d, J=8.24 Hz), 5.45 (2H, s), 4.09 (3H, s).

Workup

  1. additionA flask containing
  2. customwas flushed with nitrogen
  3. additionTHF (12 mL) was added
  4. additionThe reaction was diluted with EtOAc
  5. washwashed with water, sat. aq. Na2CO3 solution, brine
  6. dry with materialdried with sodium sulfate
  7. customThe solvent was removed
  8. filtrationFiltration
  9. washwashing with EtOAc

Sources & evidence

ORD record
ord-5246eaa4d62f4165a7ff95b36851880e
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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