Water → HCID 10156184, compound

HRID 2221251Notes

Reaction equation

HRID 2221251 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][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]=[CH:18][CH:17]=4)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[C:24](Cl)(=[O:28])[C:25](Cl)=[O:26].[OH2:30]>>[F:1][C:2]1[CH:23]=[CH:22][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]=[CH:18][CH:17]=4)=[CH:13][CH:14]=3)[C:9]([C:24](=[O:28])[C:25]([OH:30])=[O:26])=[CH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 22032946HCID 22032946, compound

Product 1

HCID 10156184HCID 10156184, compound

Procedure

The title compound was prepared from 1-(4-fluorobenzyl)-5-phenyl-1H-indole and oxalyl chloride in substantially the same manner, as described in Step 3 of Example 25. The product was obtained as a light brown solid, mp: 165-166° C. Mass spectrum (ESI, [M+H]+) m/z 374. 1HNMR (400 MHz, DMSO-d6): δ 13.54 (br s, 1H), 8.73 (s, 1H), 8.42 (s, 1H), 7.68 (d, 1H, J=8.5 Hz), 7.64 (d, 2H, J=7.5 Hz), 7.58 (dd, 1H, J=8.6 Hz and 1.7 Hz), 7.47 (t, 2H, J=7.6 Hz), 7.39 (d, 1H, J=8.6 Hz), 7.37 (d, 1H, J=8.2 Hz), 7.34 (t, 1H, J=7.4 Hz), and 5.61 ppm (s, 2H). Elemental Analysis for C23H16FNO3.0.4 H2O: Calculated: C, 72.59; H, 4.45; N, 3.68. Found: C, 72.58; H, 4.29; N, 3.62.

Workup

  1. customThe product was obtained as a light brown solid, mp: 165-166° C

Sources & evidence

ORD record
ord-e5eea90739c6452c917e6d3fba4776a6
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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