Carbon tetrabromide → tert-Butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2173931Notes

Reaction equation

HRID 2173931 reaction equation
[CH:1]([C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([CH3:14])=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O.[C:22](Br)(Br)([Br:24])[Br:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:23][C:22]([Br:24])=[CH:1][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([CH3:14])=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 72191522tert-Butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

Product 1

HCID 86701482tert-Butyl 4-(2,2-dibromovinyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate (902 mg, 3.12 mmol) in CH2Cl2 (30 mL), CBr4 (1.55 g, 4.68 mmol) was added at 0° C. followed by PPh3 (2.45 g, 9.35 mmol). The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated and directly purified via FCC eluting with Heptane/DCM 100:0 to 0:100 to provide the title compound. MS (ESI+) m/z 446.0, 448.0, 444.0, 446.9 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdirectly purified via FCC
  3. washeluting with Heptane/DCM 100:0 to 0:100

Sources & evidence

ORD record
ord-d13ac40b17b041728b81501bde8383ea
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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