2-(Bromomethyl)pyridine hydrobromide → 1'-(pyridin-2-ylmethyl)-6-(trifluoromethoxy)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one
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].Br[C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1C1(C3=CC4OCOC=4C=C3OC1)C(=O)[NH:29]2.Br.BrCC1C=CC=CN=1.BrCC1(C(F)(F)F)CC=CO1>>[N:29]1[CH:25]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:26][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:22])[F:23])=[CH:5][C:6]=3[O:21][CH2:20]2)[C:11]1=[O:19]Participants
Reactant 4
Product 1
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 2-(bromomethyl)pyridine hydrobromide to replace 2-(bromomethyl)-2-(trifluoromethyl)furan, 1′-(pyridin-2-ylmethyl)-6-(trifluoromethoxy)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained, which was treated with 4.0 M HCl in dioxane to give the title compound (39%): mp 150-152° C.; 1H NMR (300 MHz, CD3OD) δ 8.89-8.78 (m, 1 H), 8.62-8.47 (m, 1H), 8.07-7.00 (m, 2H), 7.42-6.70 (m, 7H), 5.52-5.31 (m, 2H), 5.05 (d, 1H), 4.89 (d, 1H); 13C NMR(75 MHz, CD3OD) δ 179.4, 163.5, 153.1, 152.7, 148.2, 143.8, 142.8, 133.1, 130.6, 129.3, 127.4, 126.8, 125.7, 125.6, 125.4, 114.9, 110.4, 104.9, 82.0, 58.9, 43.0; MS (ES+) m/z 413 (M+1).
Sources & evidence
- ORD record
- ord-9d26132982344742b722cda2f5cc0cd7
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106087B2
Reaction notes
Loading…