Water → HCID 10297078, compound

HRID 2221261Notes

Reaction equation

[C:1]([C:5]1[CH:28]=[CH:27][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=4)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:29](Cl)(=[O:33])[C:30](Cl)=[O:31].[OH2:35]>>[C:1]([C:5]1[CH:28]=[CH:27][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=4)=[CH:16][CH:17]=3)[C:12]([C:29](=[O:33])[C:30]([OH:35])=[O:31])=[CH:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 962Water

HCID 65578Oxalyl chloride

HCID 22032965HCID 22032965, compound

Product 1

HCID 10297078HCID 10297078, compound

Procedure

The title compound was prepared from 1-[4-(tert-butyl)benzyl]-5-(3-methoxyphenyl)-1H-indole and oxalyl chloride in substantially the same manner, as described in Step 3 of Example 25. The product was obtained as a yellow solid, mp: 86-87° C. Mass spectrum (ESI, [M+H]+) m/z 442. 1HNMR (400 MHz, DMSO-d6): δ 13.50 (br s, 1H), 8.71 (s, 1H), 8.40 (s, 1H), 7.69 (d, 1H, J=8.55 Hz), 7.58 (d, 1H, J=8.55 Hz), 7.40-7.35(m, 3H), 7.24 (d, 2H, J=8.40 Hz), 7.20(d, 1H, J=7.64 Hz), 7.14(s, 1H), 6.93 (d, 1H, J=8.25 Hz), 5.57 (s, 2H), 3.82 (s, 3H), and 1.22 ppm (s, 9H). Elemental Analysis for C28H27NO4.0.1 H2O: Calculated: C, 75.86; H, 6.18; N, 3.16. Found: C, 75.84; H, 5.91; N, 2.98.

Workup

customThe product was obtained as a yellow solid, mp: 86-87° C

Sources & evidence

ORD record: ord-9ee8d806747c4c1fa2131995f58c3cf6
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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