Carbon tetrabromide → HCID 86701673, compound

HRID 2174051Notes

Reaction equation

HRID 2174051 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH:11]=[CH2:12])[C:8]2[N:7]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:23]=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:44](Br)(Br)([Br:46])[Br:45]>C(Cl)Cl>[Br:45][C:44]([Br:46])=[CH:23][C:3]1[C:2]([CH3:1])=[CH:10][C:9]([CH:11]=[CH2:12])=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 721921455-Methyl-1-tosyl-7-vinyl-1H-indole-4-carbaldehyde

Product 1

HCID 86701673HCID 86701673, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methyl-1-tosyl-7-vinyl-1H-indole-4-carbaldehyde (50 mg, 0.147 mmol) and PPh3 (116 mg, 0.442 mmol) in DCM (1.5 mL) at 0° C., was added CBr4 (73.3 mg, 0.221 mmol) and the reaction was warmed to room temperature. After 10 minutes the reaction mixture was loaded onto silica gel and was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) d ppm 7.76-7.91 (m, 2H) 7.43-7.61 (m, 3H) 7.17-7.43 (m, 3H) 6.63-6.70 (m, 1H) 5.59 (dd, J=17.18, 1.26 Hz, 1H) 5.27 (dd, J=10.99, 1.14 Hz, 1H) 2.28-2.35 (m, 3H) 2.18-2.28 (m, 3H).

Workup

  1. customwas purified by flash chromatography (0-50% EtOAc in heptanes)

Sources & evidence

ORD record
ord-fadc854bd15e4d598c1be1a822cb429e
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…