Water → HCID 10138964, compound

HRID 2221246Notes

Reaction equation

HRID 2221246 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=4)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[C:29](Cl)(=[O:33])[C:30](Cl)=[O:31].[OH2:35]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:18][CH:17]=4)=[CH:13][CH:14]=3)[C:9]([C:29](=[O:33])[C:30]([OH:35])=[O:31])=[CH:8]2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 22032973HCID 22032973, compound

Product 1

HCID 10138964HCID 10138964, compound

Procedure

The title compound was prepared from 1-(4-methylbenzyl)-5-[4-(trifluoromethoxy)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 yellow solid, mp: 192-193° C. Mass spectrum (ESI, [M+H]+) m/z 454. 1HNMR (400 MHz, DMSO-d6): δ 13.50 (br s, 1H), 8.70 (s, 1H), 8.42 (s, 1H), 7.77 (d, 2H, J=8.7 Hz), 7.67 (d, 1H, J=8.5 Hz), 7.58 (dd, 1H, J=8.7 Hz and 1.8 Hz), 7.45 (d, 2H, J=8.3 Hz), 7.22 (d, 1H, J=7.9 Hz), 7.15 (d, 2H, J=8.1 Hz), 5.57 (s, 2H), and 2.25 ppm (s, 3H). Elemental Analysis for C25H18F3NO4.0.2 H2O: Calculated: C, 65.70; H, 4.06; N, 3.06. Found: C, 65.74; H, 4.05; N, 2.94.

Workup

  1. customThe product was obtained as a yellow solid, mp: 192-193° C

Sources & evidence

ORD record
ord-edb053009cd34617af173bf882c7a734
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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