Hydrochloric Acid → HCID 10155589, compound

HRID 1791409Notes

Reaction equation

HRID 1791409 reaction equation
[F:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:20](=[O:25])[C:21]([O:23]C)=[O:22])=[CH:15][N:16]3[CH3:19])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[OH-].[Na+].O.Cl>CO>[CH3:19][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:26])[F:27])=[CH:9][CH:8]=3)[CH:18]=2)[C:14]([C:20](=[O:25])[C:21]([OH:23])=[O:22])=[CH:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22032963HCID 22032963, compound

Product 1

HCID 10155589HCID 10155589, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of methyl 2-[6-(4-trifluoromethoxyphenyl)-1 -methyl-1H-indol-3-yl]-2-oxoacetate (0.120 g, 0.318 mmol), and sodium hydroxide (1N, 1 mL, 1.0 mmol) in methanol (10 mL), was stirred at room temperature for 2.5 hours. The mixture was poured into excess water and acidified with 1N hydrochloric acid. The mixture was extracted with ethyl acetate. The organic phase was washed with water, brine and dried over anhydrous magnesium sulfate. The organic phase was evaporated to dryness and dried under vacuum at 55° C. for 12 hours to yield the title compound as a yellow solid (0.0686 g, 59.1%), mp: 233-235° C. (dec). Mass spectrum (+APCI, [M+H]+) m/z 364; 1HNMR (400 MHz, DMSO-d6): δ 13.8-14.0 (br s, 1H), 8.55 (s, 1H), 8.25 (d, 1H, J=8.3 Hz), 7.95 (d, 1H, J=1.1 Hz), 7.85-7.95 (m, 2H), 7.65 (dd, 1H, J=8.2 and 1.6 Hz), 7.45 (dd, 2H, J=8.8 Hz and 0.88 Hz), and 4.0 ppm (s, 3H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe organic phase was evaporated to dryness
  5. customdried under vacuum at 55° C. for 12 hours

Sources & evidence

ORD record
ord-6cbfadf8a16d47548e663a040fca9cd7
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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