3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole → 4-(5-nitro-1H-indol-3-yl)cyclohex-3-en-1-one
Reaction equation
CNC1CCC(C2C3C(=CC=C(NC(C4SC=CC=4)=N)C=3)NC=2)=CC1.[CH2:26]([O:28]C(=O)CN1C2C(=CC=C([N+]([O-])=O)C=2)C=C1)C.CN1[CH2:50][CH:49]=[C:48]([C:51]2[C:59]3[C:54](=[CH:55][CH:56]=[C:57]([N+:60]([O-:62])=[O:61])[CH:58]=3)[NH:53][CH:52]=2)[CH2:47][CH2:46]1>>[N+:60]([C:57]1[CH:58]=[C:59]2[C:54](=[CH:55][CH:56]=1)[NH:53][CH:52]=[C:51]2[C:48]1[CH2:47][CH2:46][C:26](=[O:28])[CH2:50][CH:49]=1)([O-:62])=[O:61]Participants
Procedure
Compound 120 (0.26 g, 0.557 mmol) was treated with 1 N aqueous HCl solution at room temperature and the resulting solution was refluxed for 2 h. The reaction was brought to room temperature, filtered and washed with water (5 mL). The solvent was evaporated and crude was recrystallised from ethanol/ether to obtain compound 121 (0.23 g, 94%) as a solid in 2:3 ratio of diastereomers. 1H NMR (DMSO-d6) δ 1.22-1.29 (m, 3H), 1.53-1.62 (m, 2H), 1.80-2.16 (m, 6H), 2.74-3.23 (m, 4H), 7.08 (d, 1H, J=8.4 Hz), 7.24-7.52 (m, 3H), 7.68-7.72 (m, 1H), 8.14-8.18 (m, 2H), 8.59 (s, 1H), 8.97-9.09 (m, 2H), 9.64 (s, 1H), 11.20, 11.27 (2s, 1H), 11.42 (s, 1H); ESI-MS m/z (%): 367 (MH+ for free base, 18), 322 (100), 184 (19), 119 (39); ESI-HRMS calculated for C21H27N4S (MH+, free base), calculated: 367.1959; observed: 367.1950.
Sources & evidence
- ORD record
- ord-80246e06ddcb43a298daa7468440b88c
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375219B2
Reaction notes
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