4-Fluorobenzyl bromide → 1'-(4-Fluorobenzyl)-9-phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

HRID 1665345Notes

Reaction equation

HRID 1665345 reaction equation
[C:1]1([C:7]2[CH:25]=[C:24]3[C:10]([C:11](=[O:27])[C:12](=[O:26])[C:13]4[S:23][CH2:22][C:16]5([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]5)[O:15][C:14]=43)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1>>[F:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][N:19]2[CH2:20][CH2:21][C:16]3([O:15][C:14]4[C:24]5[C:10]([C:11](=[O:27])[C:12](=[O:26])[C:13]=4[S:23][CH2:22]3)=[CH:9][CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:25]=5)[CH2:17][CH2:18]2)=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 582447679-Phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Product 1

HCID 576618501'-(4-Fluorobenzyl)-9-phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Procedure

Compound 148 was synthesized using 9-phenylspiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione and 1-(bromomethyl)-4-fluorobenzene and conditions outlined in procedure V. M.p.=197-198° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.95 (m, 2H), 7.87 (d, J=7.6 Hz, 1H), 7.74 (d, J=6.8 Hz, 2H), 7.60 (m, 2H), 7.52 (m, 1H), 7.34 (m, 2H), 7.10 (t, J=8 Hz, m, 2H), 3.5 (s, 2H), 3.10 (s, 2H), 2.71 (m, 2H), 2.39 (m, 2H), 2.03 (m, 2H), 1.84 (m, 2H); LCMS: 486 [M+H].

Sources & evidence

ORD record
ord-946d3eea9ce04deaa00c55e6c32258a8
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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