Sodium hydride → 3-(N-t-Butoxycarbonyl-1.2.5.6-tetrahydropyrid-4-yl)-5-(5-nitropyrid-2-yloxy)-1H-indole

HRID 1683932Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([OH:23])[CH:21]=3)[NH:16][CH:15]=2)=[CH:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=1.[H-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=4)[CH:21]=3)[NH:16][CH:15]=2)=[CH:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 66 °C

Procedure

3-(N-t-Butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-hydroxy-1H-indole and 2-chloro-5-nitropyridine were used. Sodium hydride (60% in oil) was the base, tetrahydrofuran was the reaction solvent, the reaction time was heated at reflux (66° C.) for 12 hours, and the chromatographic solvent system was diethyl ether/hexanes [1:3] to afford the title compound (78%) as a yellow foam: 1H NMR (CD3OD) δ8.88 (d, J=2.8 Hz, 1H), 8.39 (dd, J=2.8 and 9.1 Hz, 1H), 7.56 (d, J=2.1 Hz, 1H), 7.39 (d, J=8.7 Hz, 1H), 7.31 (s, 1H), 6.94-6.88 (m, 2H), 5.98 (br m, 1H), 4.88 (s, NH), 4.00 (br m, 2H), 3.59 (br t, J=5.3 Hz, 2H), 2.50 (br m, 2H), 1.44 (s, 9H); LRMS (m/z, relative intensity) 436 (M+, 4), 379 (68), 363 (16), 335 (29), 57 (100); TLC [methylene chloride ether, 1:1]: Rf =0.5.

Workup

temperaturethe reaction time was heated

Sources & evidence

ORD record: ord-d83d759ecc9543d58f8bce2de5a88981
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639752

Reaction notes

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