2-(Bromomethyl)pyridine → 5,6-dimethyl-1'-(pyridin-2-ylmethyl)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one
Reaction equation
[CH3:1][C:2]1[C:3]([CH3:27])=[CH:4][C:5]2[O:26][CH2:25][C:8]3([C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:17][CH:18]4[CH2:23][CH2:22]OCC4)[C:9]3=[O:24])[C:6]=2[CH:7]=1.[CH3:28][C:29]1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2O[N:30]=1.BrCC1C=CC=CN=1.BrCC1OC(C(F)(F)F)=CC=1>>[CH3:1][C:2]1[C:3]([CH3:27])=[CH:4][C:5]2[O:26][CH2:25][C:8]3([C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:17][C:18]4[CH:23]=[CH:22][CH:28]=[CH:29][N:30]=4)[C:9]3=[O:24])[C:6]=2[CH:7]=1Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 9 and making non-critical variations using 5,6-dimethyl-1′-(tetrahydro-2H-pyran-4-ylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one, and 2-(bromomethyl)pyridine to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, 5,6-dimethyl-1′-(pyridin-2-ylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (76%) as a colorless solid: mp 165-168° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ8.67 (d, J=6.0 Hz, 1H), 8.12-8.06 (m, 1H), 7.59-7.55 (m, 2H), 7.26-7.23 (m, 1H), 7.21-7.20 (m, 1H), 7.03-6.98 (m, 2H), 6.76 (s, 1H), 6.55 (s, 1H), 5.18 (s, 2H), 4.74 (ABq, 2H), 2.13 (s, 3H), 2.01 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ177.5, 159.1, 154.0, 146.7, 142.6, 141.5, 138.3, 132.6, 129.1, 126.7, 124.5, 124.4, 124.1, 123.7, 123.5, 111.3, 109.7, 79.5, 57.8, 43.7, 20.2, 19.2; MS (ES+) m/z 357.2 (M+1).
Sources & evidence
- ORD record
- ord-f3da2a5d93cb4549912a107f0a851372
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
Loading…