4-Fluorobenzyl bromide → 5-bromo-1'-[(5-chloro-2-thienyl)methyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 545924Notes

Reaction equation

HRID 545924 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:19][CH2:18][C:8]3([C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:10][C:9]3=[O:17])[C:6]=2[CH:7]=1.N1C2C(=CC=CC=2)C2(C3=CC4OCOC=4C=C3OC2)C1=O.[Cl:41][C:42]1[S:43][C:44]([CH2:47]Cl)=[CH:45][CH:46]=1.FC1C=CC(CBr)=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:19][CH2:18][C:8]3([C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:47][C:44]4[S:43][C:42]([Cl:41])=[CH:46][CH:45]=4)[C:9]3=[O:17])[C:6]=2[CH:7]=1

Participants

5

Reactant 4

HCID 680214-Fluorobenzyl bromideHCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 592634985-bromospiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 119980755-bromo-1'-[(5-chloro-2-thienyl)methyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Procedure

Following the procedure described in EXAMPLE 10, and making non-critical variations using 5-bromospiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and 2-chloro-5-(chloromethyl)thiophene to replace 4-fluorobenzyl bromide, the title compound was obtained (95%) as a white solid: mp 140-142° C.; 1H NMR (300 MHz, CDCl3) δ 7.33-7.26 (m, 2H), 7.16-7.02 (m, 2H), 6.94 (d, 1H), 6.97-6.75 (m, 4H), 5.07-4.91 (m, 3H), 4.68 (d, 1H); MS (ES+) m/z 446.7 (M+1), 448.7 (M+1).

Sources & evidence

ORD record
ord-bc915abd68f54bc695a24a34f2315735
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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