Carbon Dioxide → HCID 9879625, compound

HRID 2221281Notes

Reaction equation

HRID 2221281 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:19]=[C:18]3[C:14]([CH:15]=[CH:16][N:17]3[CH3:20])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[C:26](=[O:28])=[O:27]>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([C:26]([OH:28])=[O:27])=[CH:16][N:17]3[CH3:20])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 22032913HCID 22032913, compoundHCID 178418339Butyllithium

Product 1

HCID 9879625HCID 9879625, compoundYield 10.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(4-tert-Butyl-phenyl)-1-methyl-1H-indole-3-carboxylic acid was prepared from 6-(4-tert-butyl-phenyl)-1-methyl-1H-indole (0.541 g, 2.05 mmol), n-butyllithium (0.98 mL, 2.5 mmol), crushed dry ice (3 g, 70 mmol) in dry THF (10 mL) according to the procedure described in Example 60. Purification by flash chromatography using 10-50% ethyl acetate in hexane and 100% ethyl acetate as eluants afforded the title compound as a light yellow solid (0.0675 g, 10.7%), mp: 236-238° C. (dec.). Mass spectrum (−APCI, [M−H]−) m/z 306. 1HNMR (400 MHz, DMSO-d6): δ 12.8-13.0 (br s, 1H), 7.8 (s, 1H), 7.65-7.7 (m, 3H), 7.45-7.5 (m, 2H), 7.4 (dd, 1H, J=8.3 Hz and 1.6 Hz), 7.2 (d, 1H, J=0.75 Hz), 4.05 (s, 3H) and 1.35 ppm (s, 9H). Elemental Analysis for C20H21NO2: Calculated: C, 78.15; H, 6.89; N, 4.56. Found: C, 77.82; H, 6.89; N, 4.42.

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-7f8864abfbcd4f9c9c7a9a919f742414
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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