Dimethylformamide → 6-Fluoro-5-(4-methoxy-phenyl)-1H-indole-3-carbaldehyde

HRID 338312Notes

Reaction equation

HRID 338312 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[OH-].[Na+].CN([CH:29]=[O:30])C>>[F:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:29]=[O:30])=[CH:12][NH:13]2)=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 86698658HCID 86698658, compound

Product 1

HCID 866986596-Fluoro-5-(4-methoxy-phenyl)-1H-indole-3-carbaldehydeYield 65%

Procedure

Phosphorous oxychloride (185.0 mg, 1.20 mmol) was added to DMF (2 mL) at 0° C. and the reaction mixture was stirred for 15 minutes. To this solution was added 6-fluoro-5-(4-methoxy-phenyl)-1H-indole (147.0 mg, 0.61 mmol) in DMF (2 mL) and the reaction mixture was stirred at 95° C. for 20 minutes. The reaction mixture was cooled to room temperature, treated with 1N aqueous NaOH (3 mL) and heated to 100° C. for 1 minute. The reaction mixture was cooled to room temperature and filtered. The collected solids were air dried to give the title compound (106 mg, 65% yield). MS (ES+) 270.2 (M+1)+.

Workup

  1. stirringthe reaction mixture was stirred at 95° C. for 20 minutes
  2. temperatureheated to 100° C. for 1 minute
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-41c6c495b1014d2f85643755e7a6670b
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

Loading…