2-(Bromomethyl)tetrahydro-2H-pyran → 1'-[(2-isopropyl-1,3-thiazol-5-yl)methyl]-7'-(trifluoromethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one
Reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]([CH:8]([CH3:10])[CH3:9])=[N:5][CH:4]=1.BrCC1CCCCO1.[F:19][C:20]([F:43])([F:42])[C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:29]=1[NH:28][C:27](=[O:30])[C:26]12[C:34]2=[CH:35][C:36]3[O:40][CH2:39][O:38][C:37]=3[CH:41]=[C:33]2[O:32][CH2:31]1>>[CH:8]([C:6]1[S:7][C:3]([CH2:2][N:28]2[C:29]3[C:25](=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]([F:42])([F:19])[F:43])[C:26]3([C:34]4=[CH:35][C:36]5[O:40][CH2:39][O:38][C:37]=5[CH:41]=[C:33]4[O:32][CH2:31]3)[C:27]2=[O:30])=[CH:4][N:5]=1)([CH3:10])[CH3:9]Participants
Reactant 3
Product 1
Procedure
Following the procedure as described in EXAMPLE 4 and making non-critical variations using 5-chloromethyl-2-(isopropyl)thiazole to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 7′-(trifluoromethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-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′-[(2-isopropyl-1,3-thiazol-5-yl)methyl]-7′-(trifluoromethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one was obtained (51%) as a colorless solid: mp 101-103° C.; 1H NMR (300 MHz, DMSO-d6) δ7.61 (d, J=8.1 Hz, 1H), 7.48 (d, J=6.8 Hz, 1H), 7.23 (dd J=7.8, 7.8 Hz, 1H), 7.18 (s, 1H), 6.69 (s, 1H), 6.48 (s, 1H), 5.91 (s, 2H), 5.08 (ABq, 2H), 4.77 (ABq, 2H), 3.21-3.16 (m, 1H), 1.22 (d, J=6.9 Hz, 6H); 13C NMR (75 MHz, DMSO-d6) δ178.7, 177.4, 156.0, 150.7, 149.0, 142.3, 140.7, 135.6, 128.7, 125.7, 124.5 (d), 123.6, 119.8, 113.3, 111.5 (m), 103.9, 101.9, 93.8, 80.8, 56.6, 43.3, 32.8, 23.3; MS (ES+) m/z 489.4 (M+1).
Sources & evidence
- ORD record
- ord-4db9655e37334d27a6079eefc192b885
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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