Water → HCID 10298714, compound

HRID 2221263Notes

Reaction equation

HRID 2221263 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][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:31](Cl)(=[O:35])[C:32](Cl)=[O:33].[OH2:37]>>[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH:20]=[CH:21][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:23][CH:24]=4)=[CH:16][CH:17]=3)[C:12]([C:31](=[O:35])[C:32]([OH:37])=[O:33])=[CH:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 22032921HCID 22032921, compound

Product 1

HCID 10298714HCID 10298714, compound

Procedure

The title compound was prepared from 1-[4-(tert-butyl)benzyl]-5-[4-(tert-butyl)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: 111-112° C. Mass spectrum (ESI, [M+H]+) m/z 468; 1HNMR (400 MHz, DMSO-d6): δ 13.50 (br s, 1H), 8.70 (s, 1H), 8.40 (s, 1H), 7.68 (d, 1H, J=8.55 Hz), 7.58-7.54(m, 3H), 7.48 (d, 2H, J=8.40 Hz), 7.36 (d, 2H, J=8.25 Hz), 7.25 (d, 2H, J=8.40 Hz), 5.56 (s, 2H), 1.31 (s, 9H), and 1.22 ppm (s, 9H). Elemental Analysis for C31H33NO3.0.2 H2O: Calculated: C, 79.02; H, 7.14; N, 2.97. Found: C, 78.97; H, 7.22; N, 2.90.

Workup

  1. customThe product was obtained as a light brown solid, mp: 111-112° C

Sources & evidence

ORD record
ord-a9f0612a33b8484e852a83a4d3bc0172
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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