Diethyl Ether → HCID 70981313, compound

HRID 1475462Notes

Reaction equation

HRID 1475462 reaction equation
[C:1]([Cu])#[N:2].Br[C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH3:23])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10][N:11]2[C:14](=[O:16])[CH3:15])=[CH:7][CH:6]=1.CCOCC>CN1C(=O)CCC1>[C:14]([N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([C:1]#[N:2])[CH:13]=2)[C:9]([CH3:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10]1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70980521HCID 70980521, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 70981313HCID 70981313, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
175 °C

Procedure

CuCN (179 mg, 2 mmol) was added to a solution of 1-(6-bromo-3-methyl-3-phenyl-2,3-dihydro-indol-1-yl)-ethanone (330 mg, 1 mmol) in NMP (5 mL). The reaction was stirred at 175° C. for 16 h. Et2O was added to the mixture and the solid was filtered off. The filtrate was washed with 2 M aqueous HCl and saturated aqueous NaHCO3. The solvent was removed in vacuo to give the title compound (250 mg) as a brown solid. MS: [M+H]+=277.

Workup

  1. filtrationthe solid was filtered off
  2. washThe filtrate was washed with 2 M aqueous HCl and saturated aqueous NaHCO3
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d5a0c7df34094ea7b081153019951f22
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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