Carbon Dioxide → HCID 10199737, compound

HRID 2221282Notes

Reaction equation

HRID 2221282 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:30](=[O:32])=[O:31]>C1COCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([Cl:24])[CH:18]=3)=[CH:14][CH:15]=2)[C:10]([C:30]([OH:32])=[O:31])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 22032933HCID 22032933, compoundHCID 178418339Butyllithium

Product 1

HCID 10199737HCID 10199737, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-5-(3-chloro-4-fluoro-phenyl)-1H-indole-3-carboxylic acid was prepared from 1-benzyl-5-(3-chloro-4-fluorophenyl)-1H-indole (17.99 g, 53.6 mmol), n-butyllithium (26 mL, 65 mmol), crushed dry ice (20 g, 450 mmol) in dry THF (180 mL) according to the procedure described in Example 60. Purification by HPLC using 85% acetonitrile in water as the mobile phase afforded the title compound as a light pink solid (6.51 g, 32%), mp: 189-194° C. Mass spectrum (+APCI, [M+H]+) m/z 380. 1HNMR (400 MHz, DMSO-d6): δ 13.5-13.8 (br s, 1H), 8.05 (dd, 1H, J=6.5 Hz and 2.6 Hz), 8.0 (dd, 1H, J=6.1 Hz and 2.4 Hz), 7.9 (d, 1H, J=1.5 Hz), 7.5-7.55 (m, 2H), 7.4 (dd, 1H, J=8.5 Hz and 2.0 Hz), 7.3-7.35 (m, 2H), 7.2-7.25 (m, 3H), 6.55 (dd, 1H, J=3.2 Hz and 0.75 Hz) and 5.45 ppm (s, 2H). Elemental Analysis for C22H15ClFNO2: Calculated: C, 69.57; H, 3.98; N, 3.69. Found: C, 69.87; H, 3.83; N, 3.69.

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-af7e2cbaeb2e4ddaa3ae1b4b781d75db
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

Loading…