Triphenylphosphine → 2-Bromomethyl-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole

HRID 242878Notes

Reaction equation

HRID 242878 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:8]=2[CH2:26]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:54])C(=O)C1>C(Cl)Cl>[Br:54][CH2:26][C:8]1[N:9]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[C:10]2[C:15]([C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 68156952[3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol

Product 1

HCID 681573292-Bromomethyl-3-phenyl-1-(toluene-4-sulfonyl)-1H-indoleYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol (1.31 g, 3.47 mmol) and triphenylphosphine (1.09 g, 4.16 mmol) in DCM (30 mL) at RT under a nitrogen atmosphere was added NBS (240 mg, 4.16 mmol) and stirring was continued for 2 h. Volatiles were removed under reduced pressure and the resulting residue purified by column chromatography (Si—PCC, gradient 30-100% DCM in pentane) affording the title compound as a gum (440 mg, 29%). 1H NMR (CDCl3, 400 MHz): δ 8.16 (1H, dt, J=8.48, 0.84 Hz), 7.92-7.88 (2H, m), 7.60-7.49 (4H, m), 7.48-7.37 (3H, m), 7.28-7.22 (3H, m), 5.05 (2H, s), 2.38 (3H, s)

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue purified by column chromatography (Si—PCC, gradient 30-100% DCM in pentane)

Sources & evidence

ORD record
ord-b22240a257854999bab2f5b4140def8d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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