3-Fluorobenzyl bromide → {2-[1-(3-fluoro-benzyl)-1H-indol-4-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 730577Notes

Reaction equation

HRID 730577 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:9][CH2:10][O:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CCO.[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Br>>[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:9][CH2:10][O:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][N:16]2[CH2:31][C:30]1[CH:33]=[CH:34][CH:35]=[C:28]([F:27])[CH:29]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 680073-Fluorobenzyl bromideHCID 10708626[2-(1H-indol-4-yloxy)ethyl]-methylcarbamic acid tert-butyl esterHCID 23692425Sodium hydroxide ethanol

Product 1

HCID 68813743{2-[1-(3-fluoro-benzyl)-1H-indol-4-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

Procedure

[2-(1H-Indol-4-yloxy)-ethyl]-methyl-carbamic acid tert-butyl ester was treated NaOH/EtOH followed by addition of 3-fluorobenzylbromide as described above in Step 1 of Example 5 to afford {2-[1-(3-fluoro-benzyl)-1H-indol-4-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester. MS: 299 (M−Boc+H)+.

Sources & evidence

ORD record
ord-6785193c19ef48f990244187075a148c
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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