Carbon tetrabromide → 4-(2,2-Dibromovinyl)-5,7-dimethyl-1-tosyl-1H-indole

HRID 2173986Notes

Reaction equation

HRID 2173986 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]2[N:7]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:22]=O.[C:24](Br)(Br)([Br:26])[Br:25].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:25][C:24]([Br:26])=[CH:22][C:3]1[C:2]([CH3:1])=[CH:10][C:9]([CH3:11])=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86701532HCID 86701532, compound

Product 1

HCID 867015534-(2,2-Dibromovinyl)-5,7-dimethyl-1-tosyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde (Example 46-D) (1.5 g, 4.58 mmol) and CBr4 (3.04 g, 9.16 mmol) in CH2Cl2 (50 mL) was added PPh3 (3.61 g, 13.74 mmol) at 0° C., and then the mixture was stirred at room temperature for 1 hr. The reaction mixture was directly purified by silica gel flash chromatography (heptanes/EtOAc=1/0 to 1/1) to give the title compound. MS (ESI+) m/z 483.9, 485.9, 481.9, 487.1 (M+H).

Workup

  1. customThe reaction mixture was directly purified by silica gel flash chromatography (heptanes/EtOAc=1/0 to 1/1)

Sources & evidence

ORD record
ord-53b00e6d5f1e4e01ab247ef935b5314f
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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