4-Nitrobenzyl bromide → HCID 69438464, compound

HRID 916183Notes

Reaction equation

HRID 916183 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1)([O-:16])=[O:15]>>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:21][C:20]2[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=2)[CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 69438464HCID 69438464, compound

Procedure

1-(4-Nitro-benzyl)-1H-indole-3-carboxylic acid methyl ester (I13220-11) was prepared from 1H-indole-3-carboxylic acid methyl ester and 4-nitrobenzyl bromide followed the procedure of Example 3 Step 1 as a yellow powder: 1H NMR (DMSO-d6) δ 3.83 (s, 3H), 5.70 (s, 2H), 7.23 (ddd, J=9.9, 4.6, 0.8 Hz, 2H), 7.47 (d, J=8.8 Hz, 2H), 7.50 (ddd, J=9.9, 4.6, 0.8 Hz, 1H), 8.05 (ddd, J=9.9, 4.6, 0.8 Hz, 1H), 8.19 (d, J=8.8 Hz, 2H), 8.40 (s, 1H); MS (ESI) m/z 311 (MH+), 309 ([M−H]−).

Sources & evidence

ORD record
ord-b9354dfdb12c474db6ee22c526683bb3
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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