2-(Bromomethyl)-5-(trifluoromethyl)furan → 1'-[(6-methoxypyridin-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]([O:19][CH3:20])=[CH:17][CH:18]=2)(=O)=O)=CC=1.BrCC1OC(C(F)(F)F)=CC=1.[NH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]2([C:44]3=[CH:45][C:46]4[O:50][CH2:49][O:48][C:47]=4[CH:51]=[C:43]3[O:42][CH2:41]2)[C:33]1=[O:52].CC1(C)COC2=CC3OCC4(C=3C=C12)C1C(=CC=CC=1)NC4=O>>[CH3:20][O:19][C:16]1[N:15]=[CH:14][C:13]([CH2:12][N:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]3([C:44]4=[CH:45][C:46]5[O:50][CH2:49][O:48][C:47]=5[CH:51]=[C:43]4[O:42][CH2:41]3)[C:33]2=[O:52])=[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-methoxypyridin-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′(1′H)-one to replace 5,5-dimethyl-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, the title compound was obtained (45%): 1H NMR (300 MHz, CDCl3) δ 8.19 (d, 1H), 7.59 (dd, 1H), 7.26-7.12 (m, 2H), 7.02 (t, 1H), 6.83 (d, 1H), 6.74 (d, 1H), 6.50 (s, 1H), 6.07 (s, 1H), 5.89-5.82 (m, 2H), 5.00-4.90 (m, 2H), 4.76 (d, 1H), 4.65 (d, 1H), 3.93 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 177.6, 163.7, 155.9, 149.0, 145.3, 142.4, 141.6, 138.9, 132.2, 129.0, 124.4, 124.1, 123.7, 119.2, 111.7, 109.0, 102.9, 101.5, 93.7, 80.4, 58.2, 53.9, 41.1; MS (ES+) m/z 403.2 (M+1).
Sources & evidence
- ORD record
- ord-1296e40e51994399b03d89fd001d4d03
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106087B2
Reaction notes
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