Triphenylphosphine → HCID 59425563, compound

HRID 907160Notes

Reaction equation

HRID 907160 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24]O)=[CH:18][CH:17]=1)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:45]N1C(=O)CCC1=O>C(Cl)Cl>[Br:45][CH2:24][CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:4]2[N:3]([CH2:1][CH3:2])[C:11]3[C:6]([C:5]=2[C:14]#[N:15])=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=3)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 59426185HCID 59426185, compound

Product 1

HCID 59425563HCID 59425563, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-6-methoxy-2-[4-(2-hydroxyethoxy)-phenyl]-1H-indole-3-carbonitrile (450 mg, 1.34 mmol), prepared as in example 1AZ, was combined with PPh3 (878 mg, 3.35 mmol) in CH2Cl2 (32 mL) at 0° C. N-bromosuccinimide (600 mg, 3.37 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with aqueous NaHCO3. The organic layer was dried and concentrated, and purified by silica gel chromatography (CH2Cl2) to yield 2-[4-(2-bromoethoxy)-phenyl]-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (506 mg, 95%), compound 253 as a white solid.

Workup

  1. washThe reaction mixture was washed with aqueous NaHCO3
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-f04fa302662249ce949cf33f1b9c9d97
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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