2-(Bromomethyl)tetrahydro-2H-pyran → HCID 46195853, compound
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.BrCC1CCCCO1.[CH3:22][C:23]1[C:27]2[CH:28]=[C:29]3[C:34]4([C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[NH:36][C:35]4=[O:43])[CH2:33][O:32][C:30]3=[CH:31][C:26]=2[O:25][N:24]=1>>[O:13]1[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:36]3[C:37]4[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:34]4([C:29]5[C:30](=[CH:31][C:26]6[O:25][N:24]=[C:23]([CH3:22])[C:27]=6[CH:28]=5)[O:32][CH2:33]4)[C:35]3=[O:43])=[CH:4][CH:5]=2)=[CH:10][CH:11]=[N:12]1Participants
Procedure
Following the procedure as described in EXAMPLE 4 and making non-critical variations using 5-(4-(bromomethyl)phenyl)isoxazole (0.20 g, 0.84 mmol) to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-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′-(4-isoxazol-5-ylbenzyl)-3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one was obtained (60%) as a colorless solid: mp 192-194° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.25 (d, J=1.8 Hz, 1H), 7.81 (d, J=8.3 Hz, 2H), 7.55 (d, J=8.2 Hz, 2H), 7.47 (d, J=8.6 Hz, 1H), 7.27-7.09 (m, 2H), 7.02-6.95 (m, 2H), 6.75 (d, J=7.8 Hz, 1H), 6.50 (d, J=1.8 Hz, 1H), 5.32 (d, J=16.2 Hz, 1H), 5.15 (d, J=9.1 Hz, 1H), 4.89 (d, J=9.1 Hz, 1H), 4.83 (d, J=16.2 Hz, 1H), 2.45 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 176.3, 169.0, 164.0, 158.2, 155.0, 150.8, 141.9, 137.4, 130.5, 129.4, 127.8, 126.8, 123.8, 123.7, 123.1, 118.0, 109.7, 108.9, 108.0, 98.9, 81.4, 56.4, 53.5, 44.1, 9.8; MS (ES+) m/z 449.9 (M+1).
Sources & evidence
- ORD record
- ord-271d86d1b33c4ec5a97dc25bdb6f111e
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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