3,4-Dimethylphenol → 8-hydroxy-8-(7-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-isopentyl-6H-thiazolo[5,4-e]indol-7(8H)-one
Reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:2]1=2.CC1C=C(O)C=CC=1C.[CH3:21][CH:22]([CH3:39])[CH2:23][CH2:24][N:25]1[C:33]2[C:28](=[C:29]3[S:36][CH:35]=[N:34][C:30]3=[CH:31][CH:32]=2)[C:27](=[O:37])[C:26]1=[O:38].C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(=O)C2=O)C=CC=CC=1>>[OH:37][C:27]1([C:9]2[C:8]([OH:11])=[CH:7][C:3]3[O:4][CH2:5][CH2:6][O:1][C:2]=3[CH:10]=2)[C:28]2[C:33](=[CH:32][CH:31]=[C:30]3[N:34]=[CH:35][S:36][C:29]3=2)[N:25]([CH2:24][CH2:23][CH:22]([CH3:21])[CH3:39])[C:26]1=[O:38]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in PREPARATION 6A, and making non-critical variations using 2,3-dihydrobenzo[b][1,4]dioxin-6-ol to replace 3,4-dimethylphenol, and 6-(3-methylbutyl)-6H-[1,3]thiazolo[5,4-e]indole-7,8-dione to replace 1-(diphenylmethyl)-1H-indole-2,3-dione, 8-hydroxy-8-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-6-(3-methylbutyl)-6,8-dihydro-7H-[1,3]thiazolo[5,4-e]indol-7-one was obtained (46%): 1H NMR (300 MHz, CDCl3) δ9.00 (s, 1H), 8.80 (s, 1H), 7.96 (d, J=8.5 Hz, 1H), 7.27 (s, 1H), 7.20 (d, J=8.5 Hz, 1H), 6.55 (s, 1H), 4.15 (s, 4H), 3.81-3.59 (m, 2H), 1.79-1.55 (m, 1H), 1.56-1.42 (m, 2H), 0.93 (d, J=6.6 Hz, 6H); MS (ES+) m/z 427.0 (M+1).
Sources & evidence
- ORD record
- ord-9f6abc75da484a16b408fe8e4315549c
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916580B2
Reaction notes
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