1-(diphenylmethyl)-3-(2-hydroxy-4-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one → 6'-isopentyl-3,7-dihydro-2H-spiro[benzofuro[5,6-b][1,4]dioxine-8,8'-thiazolo[5,4-e]indol]-7'(6'H)-one
Reaction equation
[OH:1][C:2]1[C:3]([CH:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]4[N:23]=[CH:22][S:21][C:19]4=3)[N:14]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:13]2=[O:29])=[CH:4][C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[C:30]1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(C3C=C(C)C(OC)=CC=3O)C2=O)C=CC=CC=1>>[CH2:24]([N:14]1[C:15]2[C:20](=[C:19]3[S:21][CH:22]=[N:23][C:18]3=[CH:17][CH:16]=2)[C:12]2([C:3]3=[CH:4][C:5]4[O:10][CH2:9][CH2:8][O:7][C:6]=4[CH:11]=[C:2]3[O:1][CH2:30]2)[C:13]1=[O:29])[CH2:25][CH:26]([CH3:27])[CH3:28]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure as described in EXAMPLE 2 and making non-critical variations using 8-(7-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-isopentyl-6H-thiazolo[5,4-e]indol-7(8H)-one to replace 1-(diphenylmethyl)-3-(2-hydroxy-4-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one, 6′-isopentyl-3,7-dihydro-2H-spiro[benzofuro[5,6-b][1,4]dioxine-8,8′-thiazolo[5,4-e]indol]-7′(6′H)-one was obtained (17%) as a colorless solid: mp 169-171° C.; 1H NMR (300 MHz, CDCl3) δ8.89 (s, 1H), 8.18 (d, J=8.5 Hz, 1H), 7.19 (d, J=8.5 Hz, 1H), 6.59 (s, 1H), 6.21 (s, 1H), 4.84 (ABq, 2H), 4.30-4.17 (m, 2H), 4.17-4.08 (m, 2H), 4.03-3.89 (m, 1H), 3.90-3.75 (m, 1H), 1.91-1.51 (m, 3H), 1.04 (d, J=6.1 Hz, 6H); MS (ES+) m/z 423.1 (M+1).
Sources & evidence
- ORD record
- ord-ddf3c774b6f643fcb6935373a55e08eb
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916580B2
Reaction notes
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