4-Nitrobenzyl bromide → HCID 69436379, compound

HRID 916187Notes

Reaction equation

HRID 916187 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH: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[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH2:21][C:20]2[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 69436379HCID 69436379, compound

Procedure

1-(4-Nitrobenzyl)-1H-indole-6-carboxylic acid methyl ester was prepared from 1H-indole-6-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 3.85 (s, 3H), 5.75 (s, 2H), 6.66(dd, J=3.1, 0.6 Hz, 1H), 7.34 (d, J=8.7 Hz, 2H), 7.60 (t, J=2.8 Hz, 1H), 7.79 (d, J=3.1 Hz, 1H), 8.07 (s, 1H), 8.15 (s, 1H), 8.19 (d, J=8.8 Hz, 1H), 8.28 (d, J=8.7 Hz, 2H); MS (ESI) m/z 311 (MH+); 309 ([M−H]−).

Sources & evidence

ORD record
ord-d9f0eb0384404e6bb34fa2a2f43c7c83
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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