2-(Bromomethyl)tetrahydro-2H-pyran → 6-methoxy-1'-(tetrahydro-2H-pyran-2-ylmethyl)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3([CH2:19][O:20][C:5]=2[CH:4]=1)[C:17]1[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=1)[NH:11][C:10]3=[O:18].CC1C2C=C3[C:33]4([C:41]5[C:36](=CC=CC=5)NC4=O)[CH2:32][O:31][C:29]3=[CH:30]C=2ON=1.BrCC1CCCCO1.BrCC1OC(C(F)(F)F)=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3([CH2:19][O:20][C:5]=2[CH:4]=1)[C:17]1[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=1)[N:11]([CH2:30][CH:29]1[CH2:36][CH2:41][CH2:33][CH2:32][O:31]1)[C:10]3=[O:18]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 9 and making non-critical variations using 6-methoxyspiro[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)tetrahydro-2H-pyran to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, 6-methoxy-1′-(tetrahydro-2H-pyran-2-ylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (54%) as a colorless foam; 1H NMR (300 MHz, CDCl3) δ 7.28 (dd, J=7.5, 7.5 Hz, 1H), 7.20-6.98 (m, 3H), 6.66-6.49 (m, 2H), 6.41-6.33 (m, 1H), 4.99-4.91 (m, 1H), 4.74-4.66 (m, 1H), 4.02-3.31 (m, 8H), 1.92-1.19 (m, 6H); MS (ES+) m/z 366.4 (M+1).
Sources & evidence
- ORD record
- ord-9a64db09c0244c9da641e3eaa9ded364
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415370B2
Reaction notes
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