4-Methyloxybenzyl chloride → 1'-(4-methoxybenzyl)-6-(trifluoromethoxy)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 645257Notes

Reaction equation

HRID 645257 reaction equation
[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]2[C:10]3([CH2:20][O:21][C:6]=2[CH:5]=1)[C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:12][C:11]3=[O:19].BrC1C=CC=C2C=1[C:27]1([C:38]3=[CH:39][C:40]4O[CH2:43][O:42][C:41]=4[CH:45]=[C:37]3OC1)C(=O)N2.COC1C=CC(CCl)=CC=1.BrCC1OC(C(F)(F)F)=CC=1>>[CH3:43][O:42][C:41]1[CH:45]=[CH:37][C:38]([CH2:27][N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]3([C:7]4[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:22])[F:23])=[CH:5][C:6]=4[O:21][CH2:20]3)[C:11]2=[O:19])=[CH:39][CH:40]=1

Participants

5

Reactant 4

HCID 699934-Methyloxybenzyl chlorideHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 119984696-(trifluoromethoxy)spiro[1-benzofuran-3,3'-indol]-2'(1'H)oneHCID 592633724'-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1H)-one

Product 1

HCID 592634911'-(4-methoxybenzyl)-6-(trifluoromethoxy)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Procedure

Following the procedure described in EXAMPLE 10.47, and making non-critical variations using 6-(trifluoromethoxy)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 4′-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and 4-methoxybenzyl chloride to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, the title compound was obtained (91%) as a white solid: mp 82-84° C.; 1H NMR (300 MHz, CDCl3) δ 7.32-6.80 (m, 9H), 6.68 (s, 2H), 5.06 (d, 1H), 5.03 (d, 1H), 4.80 (d, 1H), 4.77 (d, 1H), 3.80 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 171.1, 161.8, 159.4, 150.5, 142.3, 132.0, 129.2, 128.9, 127.7, 124.1, 124.0, 123.7, 122.2, 118.8, 114.4, 114.1, 109.7, 104.3, 80.9, 57.6, 55.4, 43.9; MS (ES+) m/z 442 (M+1).

Sources & evidence

ORD record
ord-f8eb60f58dbf42b995925e7e7d154934
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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