Triethylamine → 3-(N-t-Butoxycarbonylpiperid-4-yl)-5-(3-nitropyrid-2-ylamino)-1H-indole

HRID 1683930Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.Cl[C:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[CH:27][N:26]=1.C(N(CC)CC)C.O1CCOCC1>C(OCC)(=O)C>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:25]4[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[CH:27][N:26]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 101 °C

Procedure

5-Amino-3-(N-t-butoxycarbonylpiperid-4-yl)-1H-indole and 2-chloro-3-nitropyridine were used. Triethylamine was the base, dioxane was the reaction solvent, the reaction was heated at reflux (101° C.) for 5 hours, and the chromatographic solvent system was ethyl acetate [30-40%] in hexanes to afford the title compound (70%) as a dark red foam: 1H NMR (CDCl3) δ155.8, 155.0, 151.6, 135.5, 134.6, 129.4, 126.9, 121.3, 120.8, 119.8, 114.8, 113.1, 111.5, 79.4, 44.5, 33.6, 32.8, 28.5. Anal. calcd. for C23H27N5O4.1/4 C4H8O2 [ethyl acetate]: C, 62.73; H, 6.36; N, 15.24. Found: C, 62.51; H, 6.08; N, 15.21.

Workup

temperaturethe reaction was heated

Sources & evidence

ORD record: ord-126bd68830f146afbd49eee0f66423b7
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639752

Reaction notes

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