Ethanol → HCID 22032931, compound

HRID 2221197Notes

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:21](Cl)(=[O:25])[C:22](Cl)=[O:23].[CH2:27]([OH:29])[CH3:28]>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:19]=[C:18]3[C:14]([C:15]([C:21](=[O:25])[C:22]([O:29][CH2:27][CH3:28])=[O:23])=[CH:16][N:17]3[CH3:20])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 702Ethanol

HCID 65578Oxalyl chloride

HCID 22032913HCID 22032913, compound

Product 1

HCID 22032931HCID 22032931, compound

Procedure

Ethyl 2-{6-[4-(tert-butyl)phenyl]-1-methyl-1H-indol-3-yl}-2-oxoacetate was prepared from 6-[4-(tert-butyl)phenyl]-1-methyl-1H-indole (0.230 g, 0.874 mmol), oxalyl chloride (0.16 mL, 1.8 mmol), and ethanol (2 mL) following the procedure described in Step 3 of Example 1. The compound was purified by HPLC using 30% ethyl acetate in hexane as the mobile phase and dried for 20 minutes at 60° C. to yield a light yellow solid (0.141 g, 44%). 1HNMR (300 MHz, DMSO-d6): δ 8.5 (s, 1H), 8.2 (d, 1H, J=8.3 Hz), 7.9 (s, 1H), 7.7 (d, 2H, J=7.5 Hz), 7.65 (d, 1H, J=9.0 Hz), 7.5 (d, 2H, J=7.5 Hz), 4.35 (q, 2H, J=7.5 Hz), 3.95 (s, 3H), and 1.3-1.4 ppm (m, 12H).

Workup

customThe compound was purified by HPLC
customdried for 20 minutes at 60° C.

Sources & evidence

ORD record: ord-0e4be08120a149a9b101033e4bd1e675
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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