Carbon Dioxide → HCID 10267928, compound

HRID 1791504Notes

Reaction equation

HRID 1791504 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[CH:9]=2)[CH:4]=[CH:3]1.C([Li])CCC.[C:26](=[O:28])=[O:27]>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=3)[CH:9]=2)[C:4]([C:26]([OH:28])=[O:27])=[CH:3]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 22032934HCID 22032934, compoundHCID 178418339Butyllithium

Product 1

HCID 10267928HCID 10267928, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-methyl-6-(4-trifluoromethyl-phenyl)-1H-indole (0.483 g, 1.75 mmol) in dry THF (10 mL) at −78° C. was added n-butyllithium (0.84 mL, 2.1 mmol). The reaction mixture was stirred under nitrogen at −78° C. for 30 minutes then at −50 to −40° C. for 30 minutes. It reaction temperature was cooled to −78° C. and crushed dry ice (3.5 g, 80 mmol) was added. The reaction mixture was stirred overnight at room temperature. It was then concentrated and partitioned in 2N hydrochloric acid and 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 using 10-50% ethyl aceate in hexane as an eluant. The title compound was obtained as a yellow solid (0.108 g, 19%), mp: 237-239° C. (dec). Mass spectrum (−APCI, [M−H]−) m/z 318. 1HNMR (400 MHz, DMSO-d6): δ 12.8-13.2 (br s, 1H), 8.0 (d, 2H, J=8.1 Hz), 7.95 (s, 1H), 7.75-7.85 (m, 3H), 7.5 (dd, 1H, J=8.3 and 1.5 Hz), 7.25 (s, 1H), and 4.10 ppm (s, 3H).

Workup

  1. waitat −50 to −40° C. for 30 minutes
  2. customIt reaction temperature
  3. temperaturewas cooled to −78° C.
  4. additionwas added
  5. stirringThe reaction mixture was stirred overnight at room temperature
  6. concentrationIt was then concentrated
  7. custompartitioned in 2N hydrochloric acid
  8. washThe organic phase was washed with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated to dryness
  11. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-93b4e1e9211d4d059eda2a8ed161a707
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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