Methane → HCID 12649796, compound

HRID 917990Notes

Reaction equation

HRID 917990 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]3[CH2:18][NH:19][CH2:20][C:5]=3[C:4]=2[CH:3]=1.[Cl:21][CH2:22][CH2:23][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=[O:26].[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+].C>CN(C)C=O>[ClH:21].[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[C:6]3[CH2:18][N:19]([CH2:22][CH2:23][CH2:24][C:25](=[O:26])[C:27]4[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=4)[CH2:20][C:5]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 297MethaneHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 126497827-Fluoro-4-(4-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[3,4-b]indole

Product 1

HCID 12649796HCID 12649796, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Fluoro-4-(p-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[3,4-b]indole (6.02 g.; 22.2 m moles), 6.7 g. (33.3 m moles) of γ-chloro-p-fluorobutyrophenone, 4.28 g. (23.4 m moles) of potassium iodide and 7.05 g. (66.6 m moles) of sodium carbonate in 175 ml. of dimethylformamide is heated to 90° C. for 8 hrs. and then allowed to stir at room temperature overnight. The mixture is heated again to 90° C., treated with a gram of decolorizing charcoal, filtered and the filtrate poured into ice and water. The suspension is extracted with chloroform and the combined extracts dried and evaporated to 10.5 g. of crude product. The residue is chromatographed on 200 g. of silica gel using 3:1 diethyl ether-ethanol as the eluate, each fraction comprising 30-40 ml. The desired product, isolated from fractions 6-14, is converted to the hydrochloride salt, 1.75 g., and subsequently recrystallized from acetonitrile-methanol, 850 mg., m.p. 175°-179° C.

Workup

  1. temperatureThe mixture is heated again to 90° C.
  2. filtrationfiltered
  3. additionthe filtrate poured into ice and water
  4. extractionThe suspension is extracted with chloroform
  5. customthe combined extracts dried
  6. customevaporated to 10.5 g
  7. customThe residue is chromatographed on 200 g

Sources & evidence

ORD record
ord-2bcb094b4eb54b12bb28247580094909
Source dataset
uspto-grants-1976_07
Patent number
US03968231

Reaction notes

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