6-Benzyloxy-5-fluoro-1H-indole → 2-(6-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

HRID 1404081Notes

Reaction equation

HRID 1404081 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([C:19](=[O:25])[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C=C2C(C=CN2)=CC=1F)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:14]2[C:15]([C:11]([C:19](=[O:25])[C:20]([N:22]([CH3:23])[CH3:24])=[O:21])=[CH:12][NH:13]2)=[CH:16][C:17]=1[F:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 583039226-Benzyloxy-5-fluoro-1H-indoleHCID 669271792-(4-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

Product 1

HCID 583039052-(6-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamideYield 82%

Procedure

Following the procedure used to prepare compound 1-6a (step 5, scheme 1), compound 4-3 gave compound 4-4 in 82% yield as a white solid. 1H NMR (CDCl3, 300 MHz) □ 3.06 (s, 3H), 3.08 (s, 3H), 5.14 (s, 2H), 6.94 (d, 1H, J=6.9), 7.32-7.47 (m, 5H), 7.82 (d, 1H, J=3.0), 8.05 (d, 1H, J=11.3), 8.96 (bs, 1H). APCI [M+1]: 386.2.

Sources & evidence

ORD record
ord-3f34a2480aa54dd08de8ec2c112d8c4b
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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