2-(Bromomethyl)tetrahydro-2H-pyran → 1'-(pyridin-2-ylmethyl)spiro[furo[2,3-g]quinoxaline-8,3'-indol]-2'(1'H)-one
Reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.BrCC1CCCCO1.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([C:38]3[CH:37]=[C:36]4[C:31]([N:32]=[CH:33][CH:34]=[N:35]4)=[CH:30][C:29]=3[O:28][CH2:27]2)[C:19]1=[O:39]>>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([C:38]3[CH:37]=[C:36]4[C:31]([N:32]=[CH:33][CH:34]=[N:35]4)=[CH:30][C:29]=3[O:28][CH2:27]2)[C:19]1=[O:39]Participants
Procedure
Following the procedure as described in EXAMPLE 4 and making non-critical variations using 2-(bromomethyl)pyridine hydrobromide to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 7H-spiro[furo[2,3-g]quinoxaline-8,3′-indolin]-2′-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, 1′-(pyridin-2-ylmethyl)spiro[furo[2,3-g]quinoxaline-8,3′-indol]-2′(1′H)-one was obtained (93%) as a pale orange solid: mp 232-233° C.; 1H NMR (300 MHz, CDCl3) δ8.64 (m, 1H), 8.59 (d, J=1.5 Hz, 1H), 8.44 (d, J=1.5 Hz, 1H), 8.05 (d, J=9.3 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.77-7.67 (m, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.28-7.17 (m, 2H), 7.10 (d, J=7.2 Hz, 1H), 6.96 (t, J=7.5 Hz, 1H), 6.84 (d, J=7.8 Hz, 1H), 5.56 (d, J=16.5 Hz, 1H), 5.25 (d, J=9.0 Hz, 1H), 4.97 (d, J=9.0 Hz, 1H), 4.91 (d, J=16.5 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ177.2, 162.5, 155.9, 149.4, 144.9, 142.3, 142.1, 139.8, 139.8, 136.9, 132.6, 132.4, 128.8, 123.3, 123.2, 122.6, 121.9, 121.4, 116.6, 109.6, 82.6, 57.7, 46.5; MS (ES+) m/z 381.2 (M+1).
Sources & evidence
- ORD record
- ord-f85bfc2d1ad5407eaa849718857d0141
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415370B2
Reaction notes
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