Carbon tetrabromide → 7-Chloro-4-(2,2-dibromovinyl)-5-methyl-1-tosyl-1H-indole

HRID 2174048Notes

Reaction equation

HRID 2174048 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=2[C:5]([CH:21]=O)=[C:4]([CH3:23])[CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:43](Br)(Br)([Br:45])[Br:44]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([CH:21]=[C:43]([Br:45])[Br:44])=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 72192144HCID 72192144, compound

Product 1

HCID 867016717-Chloro-4-(2,2-dibromovinyl)-5-methyl-1-tosyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-5-methyl-1-tosyl-1H-indole-4-carbaldehyde (48 mg, 0.138 mmol) and PPh3 (109 mg, 0.414 mmol) in DCM (1.4 mL) at 0° C., was added CBr4 (68.6 mg, 0.207 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) δ ppm 8.00 (d, J=3.79 Hz, 1H) 7.88 (s, 1H) 7.73 (m, J=8.59 Hz, 2H) 7.42 (m, J=7.83 Hz, 2H) 7.23 (s, 1H) 6.71 (d, J=3.79 Hz, 1H) 2.37 (s, 3H) 2.23 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-7d8fac92fc504c1bb117c29e9ba25792
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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