Ethyl 5-methoxyindole-2-carboxylate → HCID 21964306, compound

HRID 2212167Notes

Reaction equation

HRID 2212167 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2.[C:17]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[C:7]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:27][CH:28]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

3

Reactant 2

HCID 20926Ethyl 5-methoxyindole-2-carboxylateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

Product 1

HCID 21964306HCID 21964306, compound

Procedure

The title compound was prepared from ethyl 5-methoxy-1H-indole-2-Carboxylate and 4-(tert-butyl) benzyl bromide in substantially the same manner, as described in step 1 of Example 1. The product was obtained as a solid. Mass spectrum (ESI, [M−H]−) m/z 364. 1H NMR (400 MHz, DMSO-d6) δ 7.48 (d, 1H, J=9.20 Hz), 7.27 (s, 1H), 7.24 (d, 2H, J=7.18 Hz), 7.16 (d, 1H, J=2.44 Hz), 6.96–6.92 (m, 3H), 5.77 (s, 2H), 4.28 (q, 2H), 3.76 (s, 3H), 1.28 (s, 3H), and 1.20 ppm (s, 9H).

Workup

  1. customThe product was obtained as a solid

Sources & evidence

ORD record
ord-120f3e3fcefd49bdb3382b7c3d77c2d0
Source dataset
uspto-grants-2006_09
Patent number
US07101903B2

Reaction notes

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