Dimethylformamide → HCID 19029244, compound

HRID 865648Notes

Reaction equation

HRID 865648 reaction equation
CN(C=O)C.[C:6](Cl)(=[O:10])[C:7](Cl)=O.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:27]=[C:26]3[C:22](C=[CH:24][NH:25]3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>CO.C(Cl)Cl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:27]=[C:26]3[C:22]([C:7]([CH:6]=[O:10])=[CH:24][NH:25]3)=[CH:21][CH:20]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 111066586-(4-FLUOROPHENYL)INDOLE

Product 1

HCID 19029244HCID 19029244, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of DMF (5.0 mL, 64 mmol) and CH2Cl2 (120 mL) was added oxalyl chloride (2.1 mL, 24 mmol). The mixture was stirred for 45 minutes at ambient temperature and then was decanted into a solution of 6-(4-fluorophenyl)indole (5.1 g, 24 mmol), which was prepared as described in International Application Number PCT/US92/05890 (4 Feb. 1993). The reaction mixture was stirred for 90 minutes at ambient temperature and the imminium salt was isolated by filtration. The solids were dissolved in methanol (150 mL) and saturated aqueous NaHCO3 (200 mL) was added. The resulting precipitate was filtered and dried in a vacuum oven to give 6-(4-fluorophenyl)indole-3-carboxaldehyde (4.14 g, 72%) as a tan powder.

Workup

  1. customwas prepared
  2. stirringThe reaction mixture was stirred for 90 minutes at ambient temperature
  3. customthe imminium salt was isolated by filtration
  4. filtrationThe resulting precipitate was filtered
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-f84ee2ed9382425185fb53b615b0d7fb
Source dataset
uspto-grants-1996_10
Patent number
US05567711

Reaction notes

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