Ammonium Chloride → HCID 22467252, compound

HRID 381329Notes

Reaction equation

HRID 381329 reaction equation
C[Mg]Br.[Br:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1.Br[CH:15]([C:20]1[CH:28]=[C:27]([O:29][CH3:30])[C:23]2[O:24][CH2:25][O:26][C:22]=2[CH:21]=1)[C:16]([O:18][CH3:19])=[O:17].[Cl-].[NH4+]>C1(C)C=CC=CC=1.C(OCC)C>[Br:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:15]([C:20]3[CH:28]=[C:27]([O:29][CH3:30])[C:23]4[O:24][CH2:25][O:26][C:22]=4[CH:21]=3)[C:16]([O:18][CH3:19])=[O:17])=[CH:10][NH:11]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 6764936-BromoindoleHCID 22467249HCID 22467249, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22467252HCID 22467252, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Methyl magnesium bromide (3.6 ml of 3 M solution in diethyl ether) was added dropwise to a stirred solution of 6-bromo-indole (2.13 g, 10.9 mmol) in toluene (20 ml) under a nitrogen atmosphere. After 20 minutes the reaction mixture was transferred via a cannula, over ˜10 minutes, to a stirred solution of methyl 2-bromo-2-(7-methoxy-1,3-benzodioxol-5-yl)acetate (from step (b), 2.2 g, 7.26 mmol) in toluene (20 ml) at ambient temperature. After a further 2 hours the mixture was poured into a mixture of diethyl ether and aqueous ammonium chloride. The organic layer was separated and dried (magnesium sulphate), and the solvent was removed in vacuo. The residue was flash chromatographed using dichloromethane as eluant to give the subtitle compound (2.7 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (magnesium sulphate)
  3. customthe solvent was removed in vacuo
  4. customchromatographed

Sources & evidence

ORD record
ord-9370986aab7a44b3bb3b1db7d9024dd1
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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