2-(Bromomethyl)tetrahydro-2H-pyran → 1'-(pyridin-2-ylmethyl)-4'-quinolin-3-yl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-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.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20]([C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[C:30]2([C:49]4[C:40](=[CH:41][C:42]5[O:47][CH2:46][CH2:45][O:44][C:43]=5[CH:48]=4)[O:39][CH2:38]2)[C:31](=[O:37])[NH:32]3)[CH:19]=1>>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][N:32]1[C:33]2[C:29](=[C:28]([C:20]3[CH:19]=[N:18][C:27]4[C:22]([CH:21]=3)=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:36]=[CH:35][CH:34]=2)[C:30]2([C:49]3[C:40](=[CH:41][C:42]4[O:47][CH2:46][CH2:45][O:44][C:43]=4[CH:48]=3)[O:39][CH2:38]2)[C:31]1=[O:37]Participants
Reactant 3
Product 1
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 4′-quinolin-3-yl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-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)-4′-quinolin-3-yl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (73%) as a colorless solid: mp 228-230° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 10.70 (s, 1H), 7.42-7.32 (m, 2H), 7.26 (t, J=7.8 Hz, 1H), 7.13-7.05 (m, 1H), 6.96-6.90 (m, 3H), 6.79-6.70 (m, 5H), 6.23 (s, 1H), 6.12 (s, 1H), 4.47 (d, J=9.3 Hz, 1H), 4.32 (d, J=9.3 Hz, 1H), 4.15-4.01 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 177.8, 155.4, 150.3, 149.6, 147.2, 144.8, 142.7, 138.2, 137.2, 136.4, 135.7, 131.2, 130.4, 129.2, 128.0, 126.9, 125.9, 122.9, 122.7, 121.8, 111.3, 109.5, 99.6, 64.6, 64.1, 46.3; MS (ES+) m/z 513.9 (M+1).
Sources & evidence
- ORD record
- ord-4d354a0ed7e742e8beaef96ca3659756
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415370B2
Reaction notes
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