4-Nitrobenzyl bromide → HCID 69435489, compound

HRID 916185Notes

Reaction equation

HRID 916185 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=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:6]2[CH:7]=[CH:8][N:9]([CH2:21][C:20]3[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=3)[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

3

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 69435489HCID 69435489, compound

Procedure

1-(4-Nitro-benzyl)-1H-indole-4-carboxylic acid methyl ester was prepared from 1H-indole-4-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 3.90 (s, 3H), 5.69 (s, 2H), 7.05(dd, J=3.1, 0.9 Hz, 1H), 7.22 (t, J=7.6 Hz, 1H), 7.36 (d, J=8.9 Hz, 2H), 7.75 (td, J=7.6, 3.1 Hz, 3H), 8.18 (d, J=8.9 Hz, 2H); MS (ESI) m/z 311 (MH+), 309 ([M−H]−); Anal. calcd for C17H14N2O4: C, 65.80; H, 4.55; N, 9.03. Found: C, 65.81; H, 4.50; N, 8.98.

Sources & evidence

ORD record
ord-c639e039ff1947458bc754e5181f97f5
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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