Methanol → HCID 9967433, compound

HRID 2221286Notes

Reaction equation

HRID 2221286 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[C:4]([CH2:21][C:22]#N)=[CH:3]1.[OH-:24].[K+].C[OH:27]>O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[C:4]([CH2:21][C:22]([OH:27])=[O:24])=[CH:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 22032977HCID 22032977, compound

Product 1

HCID 9967433HCID 9967433, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of [1-methyl-5-(4-trifluoromethyl-phenyl)-1H-indol-3-yl]-acetonitrile (0.230 g, 0.732 mmol), potassium hydroxide (2.16 g, 38.5 mmol), methanol (5 mL) and water (5 mL) was heated at refluxed for 24 hours. The reaction mixture was cooled to room temperature and concentrated. Water was added and the mixture was acidified with 2N hydrochloric acid. The mixture was extracted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to dryness. Purification of the residue by HPLC using 4% methanol in methylene chloride as the mobile phase afforded the title compound as a light brown solid (0.0598 g, 25%), mp 167-168° C. Mass spectrum (+APCI, [M+H]+) m/z 334. 1HNMR (400 MHz, DMSO-d6): δ 12.1-12.4 (br s, 1H), 7.9 (d, 3H, J=7.8 Hz), 7.8 (d, 2H, J=8.1 Hz), 7.55 (d, 2H, J=1.2 Hz), 7.3 (s, 1H), 3.8 (s, 3H) and 3.7 ppm (s, 2H). Elemental Analysis for C18H14F3NO2: Calculated: C, 64.86; H, 4.23; N, 4.20. Found: C, 64.88; H, 4.17; N, 4.03.

Workup

  1. temperaturewas heated
  2. temperatureat refluxed for 24 hours
  3. concentrationconcentrated
  4. additionWater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated to dryness
  9. customPurification of the residue by HPLC

Sources & evidence

ORD record
ord-7ce4cf060e7b4fb6b0983ffa59e34445
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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