Carbon tetrabromide → HCID 68535392, compound

HRID 2389353Notes

Reaction equation

HRID 2389353 reaction equation
O[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][N:12]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[O:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:44]>C(Cl)Cl>[Br:44][CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][N:12]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[O:6][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68535289HCID 68535289, compound

Product 1

HCID 68535392HCID 68535392, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[4-(hydroxymethyl)-1,3-oxazol-2-yl]-1H-indole-1-carboxylate (330 mg) and PPh3 (330 mg) in DCM (6.6 mL) was added portionwise carbon tetrabromide (418 mg) at ambient temperature and the mixture was stirred at the same temperature for 4 hours. The resulting mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography(n-hexane:EtOAc=5:1) to afford tert-butyl 4-[4-(bromomethyl)-1,3-oxazol-2-yl]-1H-indole-1-carboxylate (396 mg) as a white solid.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography(n-hexane:EtOAc=5:1)

Sources & evidence

ORD record
ord-92dee7ceb3de4b07b11dea4b692483d2
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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