Triphenylphosphine → HCID 11217658, compound

HRID 1264200Notes

Reaction equation

HRID 1264200 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][N:14]=[N+]=[N-])[CH:10]=2)[NH:5][CH:4]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][NH2:14])[CH:10]=2)[NH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 18617612HCID 18617612, compound

Product 1

HCID 11217658HCID 11217658, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.01 g (4.78 mmol) 3-cyano-5-(2-azidoethyl)indole (reference example 3) and 1.38 g (5.26 mmol) triphenylphosphine in 20 mL THF is stirred overnight to give a white precipitate. Another 20 mL THF and 1 mL distilled water is added. After stirring overnight the resulting solution is concentrated, and the residue chromatographed (10:1 CH2Cl2:7N NH3 in MeOH) to provide 0.870 g of the product as a white solid in 98% yield. 1H NMR (CD3OD): δ 2.87-2.97 (4H, m), 7.17 (1H, d, J=8 Hz), 7.45 (1H, d, J=8 Hz), 7.50 (1H, s), 7.90 (1H, s). MS (EI) m/z 185 M+, 169 (M−NH3)+, 155 (M−CH2NH2)+.

Workup

  1. customto give a white precipitate
  2. distillationAnother 20 mL THF and 1 mL distilled water
  3. additionis added
  4. concentrationis concentrated
  5. customthe residue chromatographed (10:1 CH2Cl2:7N NH3 in MeOH)

Sources & evidence

ORD record
ord-85b012ffde00467ab63bfc0996cc55bd
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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