Dichloromethane → HCID 66832123, compound

HRID 58778Notes

Reaction equation

HRID 58778 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14]([C:16]1[O:20][CH:19]=[N:18][CH:17]=1)=[O:15].[C:21]1(I)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.ClCCl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(=O)([O-])[O-].[Ag+2].O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14]([C:16]1[O:20][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:18][CH:17]=1)=[O:15]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11575IodobenzeneHCID 11776TriphenylphosphineHCID 66832046HCID 66832046, compound

Product 1

HCID 66832123HCID 66832123, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 178418647HCID 178418647, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Water (5 mL) was added to a pre-stirred mixture of N-(2-(5-chloro-1H-indol-3-yl)ethyl)oxazole-5-carboxamide intermediate 173 (0.107 g; 0.369 mmol), phenyl iodide (0.050 mL; 0.443 mmol), (1,1′-bis(diphenylphosphino) ferrocene)-dichloropalladium(II), complex with dichloromethane (0.015 g; 0.019 mmol), silver carbonate (0.204 g; 0.738 mmol) and triphenylphosphine (0.010 g; 0.037 mmol). The resulting mixture was stirred at 70° C. for 24 hours and after cooling down the mixture was partitioned between brine and dichloromethane. The two phases were separated and the aqueous layer was extracted with dichloromethane. The organic layer was dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.025 (19%) of the title compound as a yellow solid.

Workup

  1. temperatureafter cooling down the mixture
  2. customwas partitioned between brine and dichloromethane
  3. customThe two phases were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. customThe organic layer was dried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-8e662f39f86f404ea524d4ba44788077
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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