Potassium Phosphate, Tribasic → 1-tert-Butyl 6-methyl 3-phenyl-1H-indole-1,6-dicarboxylate

HRID 401711Notes

Reaction equation

HRID 401711 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=1.[CH:22]1(C2C=CC(C(N3CC(N4CCN(C(C5C=CC=CC=5)=O)CC4)C3)=O)=CC=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:22]1([C:2]2[C:10]3[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=3)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 71278271-tert-butyl 6-methyl 3-iodo-1H-indole-1,6-dicarboxylateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 497631551-{1-[(4-Cyclohexylphenyl)carbonyl]azetidin-3-yl}-4-(phenylcarbonyl)-piperazine

Product 1

HCID 596260441-tert-Butyl 6-methyl 3-phenyl-1H-indole-1,6-dicarboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-tert-butyl 6-methyl 3-iodo-1H-indole-1,6-dicarboxylate 62a (5.02 mmol, 2.016 g), phenylboronic acid 1× (7.53 mmol, 0.92 g), Pd(OAc)2 (0.402 mmol, 90 mg), Sphos 0.904 mmol, (0.37 g), and K3PO4 (10.1 mmol, 2.13 g) in toluene (10 mL) in sealed reaction vial was stirred at room temperature for 2 min and then heated at 90° C. under N2 for 4 h. The reaction mixture was quenched with EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 8% EtOAc/hexanes). The desired product was collected as a light yellow solid that was washed with small amount of hexanes to obtain 62b as a white solid.

Workup

  1. customin sealed reaction vial
  2. temperatureheated at 90° C. under N2 for 4 h
  3. customThe reaction mixture was quenched with EtOAc and water
  4. concentrationThe organic layer was concentrated
  5. custompurified by flash column chromatography (silica gel, 8% EtOAc/hexanes)
  6. customThe desired product was collected as a light yellow solid
  7. washthat was washed with small amount of hexanes

Sources & evidence

ORD record
ord-94dfe094f7244aa3b05880cb85ffedc7
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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