3-Bromophenol → 8-hydroxy-8-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-6-(4-methoxybenzyl)-6,8-dihydro-7H-[1,3]thiazolo[5,4-e]indol-7-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.BrC1C=C(O)C=CC=1.[CH3:20][O:21][C:22]1[CH:42]=[CH:41][C:25]([CH2:26][N:27]2[C:35]3[C:30](=[C:31]4[S:38][CH:37]=[N:36][C:32]4=[CH:33][CH:34]=3)[C:29](=[O:39])[C:28]2=[O:40])=[CH:24][CH:23]=1.FC(F)(F)C1OC(CN2C3C(=CC=CC=3)C(=O)C2=O)=CC=1>>[OH:39][C:29]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:30]2[C:35](=[CH:34][CH:33]=[C:32]3[N:36]=[CH:37][S:38][C:31]3=2)[N:27]([CH2:26][C:25]2[CH:41]=[CH:42][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[C:28]1=[O:40]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in PREPARATION 2A and making non-critical variations using 2,3-dihydrobenzo[b][1,4]dioxin-6-ol to replace 3-bromophenol, and 6-(4-methoxybenzyl)-6H-[1,3]thiazolo[5,4-e]indole-7,8-dione to replace 1-((5-(trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione, 8-hydroxy-8-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-6-(4-methoxybenzyl)-6,8-dihydro-7H-[1,3]thiazolo[5,4-e]indol-7-one was obtained (39%) as a colorless solid: MS (ES+) m/z 477.1 (M+1).
Sources & evidence
- ORD record
- ord-5faea20e59614db2990c424ac2a72343
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916580B2
Reaction notes
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