Methanol → HCID 22032963, compound

HRID 2221181Notes

Reaction equation

HRID 2221181 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][N:16]3[CH3:19])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[C:22](Cl)(=[O:26])[C:23](Cl)=[O:24].CO.[C:30](=O)(O)[O-:31].[Na+]>C1COCC1>[F:21][C:2]([F:1])([F:20])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:22](=[O:26])[C:23]([O:31][CH3:30])=[O:24])=[CH:15][N:16]3[CH3:19])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 22032909HCID 22032909, compound

Product 1

HCID 22032963HCID 22032963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-trifluoromethoxyphenyl)-1-methyl-1H-indole (0.304 g, 1.04 mmol) in dry THF (5 mL) under nitrogen at 0° C. was added oxalyl chloride (0.11 ml, 1.2 mmol). The reaction mixture was stirred at room temperature for 2 hour. The mixture was cooled in an ice bath. Methanol (1 mL) was added. The reaction mixture was stirred at room temperature for 1 hour then poured into excess sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated to dryness. The residue was purified by flash chromatography (Biotage apparatus) using 20-50% ethyl acetate in hexane as an eluant. The title compound was obtained as a cream-colored solid (0.196 g, 50%), mp: 152-153° C. Mass spectrum (+APCI, [M+H]+) m/z 378; 1HNMR (400 MHz, DMSO-d6): δ8.55 (s, 1H), 8.2 (d, 1H, J=8.3 Hz), 7.95 (t, 1H, J=0.77 Hz), 7.90-7.95 (m, 2H), 7.65 (dd, 1H, J=8.3 Hz and 1.5 Hz), 7.45 (d, 2H, J=8.6 Hz), 4.0 (s, 3H), and 3.9 ppm (m, 3H). Elemental Analysis for C19H14F3NO4: Calculated: C, 60.48; H, 3.74; N, 3.71. Found: C, 60.60; H, 3.86; N, 3.60.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (Biotage apparatus)

Sources & evidence

ORD record
ord-09091d3428ae4a45bd93a897d33c8169
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

Loading…