Aluminum;lithium → HCID 21964281, compound

HRID 2373480Notes

Reaction equation

[CH3:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=4)=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:23](OCC)=[O:24])=[CH:4][CH:3]=1.[Al].[Li]>>[CH3:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=4)=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:23][OH:24])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 16211445Aluminum;lithium

HCID 21964309HCID 21964309, compound

Product 1

HCID 21964281HCID 21964281, compound

Procedure

The title compound was prepared from ethyl 1-(4-methylbenzyl)5-(3-methylphenyl)-1H-indole-2-carboxylate and lithium aluminum in substantially the same manner, as described in step 3 of Example 1. The product was obtained as a white solid. Mass spectrum (ESI, [M+H]+) m/z 342. 1H NMR (400 MHz, DMSO-d6) δ 7.77 (s, 1H), 7.46 (s, 1H), 7.42 (d, 1H, J=7.79 Hz), 7.37 (d, 1H, J=8.55 Hz); 7.33 (d, 1H, J=8.56 Hz), 7.31 (d, 1H, J=7.02 Hz), 7.29 (d, 1H, J=7.48 Hz), 7.10-7.07 (m, 4H), 6.96 (d, 2H, J=7.94 Hz), 6.48 (s, 1H), 5.54 (s, 2H), 5.33 (s, 1H), 4.60 (s, 2H), 2.36 (s, 3H), and 2.23 ppm (s, 3H).

Workup

customThe product was obtained as a white solid

Sources & evidence

ORD record: ord-5a44751793944294a463b1bb0e2194f9
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459478B2

Reaction notes

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