Potassium Phosphate, Tribasic → HCID 86701700, compound

HRID 2174069Notes

Reaction equation

HRID 2174069 reaction equation
Br[C:2]1[C:10]2[C:9]([CH:11]=[O:12])=[C:8]([CH3:13])[CH:7]=[C:6]([CH3:14])[C:5]=2[N:4]([S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:3]=1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>COCCOC.C(Cl)Cl.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:13][C:8]1[CH:7]=[C:6]([CH3:14])[C:5]2[N:4]([S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:16])=[O:17])[CH:3]=[C:2]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]=2[C:9]=1[CH:11]=[O:12]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 867016993-Bromo-5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde

Product 1

HCID 86701700HCID 86701700, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 3-bromo-5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde (100 mg, 0.246 mmol), phenylboronic acid (60.0 mg, 0.492 mmol), and K3PO4 (157 mg, 0.738 mmol) in DME (1 mL)/H2O (0.5 mL), Pd(OAc)2 (5.53 mg, 0.025 mmol) and S-phos (CAS#657408-07-6) (20.21 mg, 0.049 mmol) were added the mixture was stirred at 80° C. for 15 h. The reaction mixture was cooled to room temperature and diluted with CH2Cl2 and water. The layers were partitioned. The organic layer was separated, dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel flash column chromatography [heptane/(30% EtOAc in CH2Cl2)=1/0 to 4/6] to give the title compound. MS (ESI+) m/z 404.1 (M+H).

Workup

  1. additionwere added the mixture
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe layers were partitioned
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel flash column chromatography [heptane/(30% EtOAc in CH2Cl2)=1/0 to 4/6]

Sources & evidence

ORD record
ord-43178539b2e6408694bd073248fa5859
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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