Triphenylphosphine → HCID 59425563, compound

HRID 252552Notes

Reaction equation

HRID 252552 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, is combined with PPh3 (878 mg, 3.35 mmol) in CH2Cl2 (32 mL) at 0° C. N-bromosuccinimide (600 mg, 3.37 mmol) is added in one portion. The reaction mixture is stirred at room temperature for 30 minutes. The reaction mixture is washed with aqueous NaHCO3. The organic layer is 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 is washed with aqueous NaHCO3
  2. customThe organic layer is dried
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-30579d8aea004dceb3b8925b5403a8c8
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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