Diethyl Ether → HCID 21481269, compound

HRID 917991Notes

Reaction equation

HRID 917991 reaction equation
CI.[Mg].[CH2:4](OCC)C.[ClH:9].[F:10][C:11]1[CH:19]=[CH:18][C:17]2[N:16]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:15]3[CH2:27][N:28]([CH2:30][CH2:31][CH2:32][C:33](=[O:41])[C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)[CH2:29][C:14]=3[C:13]=2[CH:12]=1>O.O1CCCC1>[ClH:9].[F:10][C:11]1[CH:19]=[CH:18][C:17]2[N:16]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[C:15]3[CH2:27][N:28]([CH2:30][CH2:31][CH2:32][C:33]([C:34]4[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=4)([OH:41])[CH3:4])[CH2:29][C:14]=3[C:13]=2[CH:12]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 12649796HCID 12649796, compound

Product 1

HCID 21481269HCID 21481269, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A methyl Grignard reagent prepared from 852 mg. (6 m moles) of methyl iodide and 144 mg. (6 m mole) of magnesium in 40 ml. of diethyl ether is divided into equal portions. To one-half is added portionwise 500 mg. (1.1 m moles) of 7-fluoro-4-(p-fluorophenyl)-2-[3-(p-fluorobenzoyl)propyl]-1,2,3,4-tetrahydropyrrolo[3,4-b]indole hydrochloride in 20 ml. of tetrahydrofuran, and the mixture allowed to stir for 1 hour. To the mixture is then added the other half of the Grignard solution, and stirring maintained for 30 min. The mix is poured into ice and water and extracted with ether. The combined ether extracts are dried over magnesium sulfate, concentrated to dryness, and the residue chromatographed on 20 g. of silica gel using 3:1 diethyl ether-ethanol as the eluate, each collecting fractions being 3 ml. Fractions 10-27 are combined and converted to the hydrochloride salt, 180 mg.

Workup

  1. additionTo one-half is added portionwise 500 mg
  2. additionTo the mixture is then added the other half of the Grignard solution
  3. stirringstirring
  4. temperaturemaintained for 30 min
  5. extractionextracted with ether
  6. dry with materialThe combined ether extracts are dried over magnesium sulfate
  7. concentrationconcentrated to dryness
  8. customthe residue chromatographed on 20 g

Sources & evidence

ORD record
ord-440dc2c481844051a6bc3d7993013f4f
Source dataset
uspto-grants-1976_07
Patent number
US03968231

Reaction notes

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