2-(Bromomethyl)-5-(trifluoromethyl)furan → 1'-[(6-methylpyridin-3-yl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one
Reaction equation
CC1C=CC(S(O[CH2:12][C:13]2[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=O)=O)=CC=1.BrCC1OC(C(F)(F)F)=CC=1.[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]2([C:43]3=[CH:44][C:45]4[O:49][CH2:48][O:47][C:46]=4[CH:50]=[C:42]3[O:41][CH2:40]2)[C:32]1=[O:51].CC1(C)COC2=CC3OCC4(C=3C=C12)C1C(=CC=CC=1)NC4=O>>[CH3:19][C:16]1[N:15]=[CH:14][C:13]([CH2:12][N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]3([C:43]4=[CH:44][C:45]5[O:49][CH2:48][O:47][C:46]=5[CH:50]=[C:42]4[O:41][CH2:40]3)[C:32]2=[O:51])=[CH:18][CH:17]=1Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 10.21, and making non-critical variations using (6-methylpyridin-3-yl)methyl 4-methylbenzenesulfonate to replace 2-bromomethyl-5-(trifloromethyl)furan, and spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1H)-one to replace 5,5-dimethyl-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, 1′-[(6-methylpyridin-3-yl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one was obtained (56%), which was treated with 2.0 M HCl in diethyl ether to give the title compound: 1H NMR (300 MHz, CD3OD) δ 8.77 (s, 1H), 8.46 (dd, 1H), 7.91 (d, 1H), 7.33 (t, 1H), 7.24-7.09 (m, 3H), 6.52 (s, 1H), 6.14 (s, 1H), 5.86 (s, 2H), 5.18 (s, 2H), 4.93-4.85 (m, 1H), 4.71 (d, 1H), 2.77 (s, 3H); 13C NMR (75 MHz, CD3OD) δ 180.0, 157.6, 155.1, 150.6, 146.6, 143.8, 142.7, 141.2, 135.7, 133.5, 130.3, 129.5, 125.3, 125.2, 120.5, 110.3, 103.8, 103.0, 94.3, 81.5, 59.7, 41.5, 19.5; MS (ES+) m/z 387.4 (M+1).
Sources & evidence
- ORD record
- ord-c5e67e569723402591fe94689c16ef23
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106087B2
Reaction notes
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