4-Nitrobenzyl bromide → HCID 69436120, compound

HRID 916181Notes

Reaction equation

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

Participants

Reactant 2

HCID 660114-Nitrobenzyl bromide

HCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 69436120HCID 69436120, compound

Procedure

1-(4-Nitro-benzyl)-1H-indole-5-carboxylic acid methyl ester was prepared from 1H-indole-5-carboxylic acid methyl ester and 4-nitrobenzyl bromide followed the procedure of Example 3 Step 1 as a yellow poder: 1H NMR (DMSO-d6) δ 3.84 (s, 3H), 5.67 (s, 2H), 6.71 (dd, J=3.2, 0.8 Hz, 1H), 7.40 (d, J=8.8 Hz, 2H), 7.54 (d, J=8.7 Hz, 1H), 7.67 (d, J=0.8 Hz, 1H), 7.73 (dd, J=8.8, 1.7 Hz, 1H), 8.19 (d, J=8.8 Hz, 2H), 8.29 (d, J=1.0 Hz, 1H); MS (ESI) m/z 311 (MH+), 309 ([M−H]−); HRMS calcd for C17H15N2O4: 311.1030; found (ESI+): 311.1021.

Sources & evidence

ORD record: ord-87d1acb5d8b44431aa9011ca378814b1
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268159B2

Reaction notes

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