Ethanol → HCID 22032981, compound

HRID 1791428Notes

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]([C:23](=[O:25])[CH3:24])=[CH:19][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:26](Cl)(=[O:30])[C:27](Cl)=[O:28].[CH2:32]([OH:34])[CH3:33]>>[C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=[C:10]3[C:26](=[O:30])[C:27]([O:34][CH2:32][CH3:33])=[O:28])=[CH:22][CH:21]=1)(=[O:25])[CH3:24]

Participants

Reactant 3

HCID 702Ethanol

HCID 65578Oxalyl chloride

HCID 220329561-[4-(1-benzyl-1H-indol-5-yl)phenyl]-1-ethanone

Product 1

HCID 22032981HCID 22032981, compound

Procedure

Ethyl 2-[5-(4-acetylphenyl)-1-benzyl-1H-indol-3-yl]-2-oxoacetate was prepared from 1-[4-(1-benzyl-1H-indol-5-yl)phenyl]-1-ethanone (0.255 g, 0.784 mmol), oxalyl chloride (0.14 mL, 1.6 mmol), and ethanol (2 mL), following the procedure described in Step 3 of Example 1. Purification by flash chromatography using 30-50% chloroform in hexane as an eluant and drying at 55° C. yielded a brownish solid (0.243 g, 73%). 1HNMR (300 MHz, DMSO-d6): δ 8.75 (s, 1H), 8.5 (s, 1H), 8.05 (d, 2H, J=9.2 Hz), 7.8 (d, 2H, J=7.7 Hz), 7.7 (q, 2H, J=8.5 Hz), 7.25-7.4 (m, 5H), 5.65 (s, 2H), 4.35 (q, 2H, J=7.2 Hz), 2.6 (s, 3H), and 1.35 ppm (t, 3H, J=7.3 Hz).

Workup

customPurification by flash chromatography
customdrying at 55° C.

Sources & evidence

ORD record: ord-6f7e945e1c1e487487f9c21e4512dfe5
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074817B2

Reaction notes

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