Nitrogen → HCID 136342125, compound

HRID 748542Notes

Reaction equation

[OH:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][N:12]=1)=[CH:8][C:7]([N+:22]([O-:24])=[O:23])=[CH:6][CH:5]=2.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.N#N.C[Al](C)C>C1C=CC=CC=1>[N:25]1([C:15]([C:14]2[CH:20]=[CH:21][C:11]([C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([N+:22]([O-:24])=[O:23])[CH:8]=4)[NH:3][C:2]=3[OH:1])=[N:12][CH:13]=2)=[O:16])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 70 °C

Procedure

Ethyl 6-(2-hydroxy-5-nitro-1H-indol-3-yl)nicotinate (0.327 g, 1.0 mmol) was suspended in benzene (13 mL) followed by the addition of morpholine (0.218 g, 2.5 mmol). The mixture was stirred (N2 atmosphere) for 5 min at 0° C. To this mixture, trimethyl aluminum (2 M solution in hexane, 2 mL, 4 mmol) was added via a syringe. After 10 min the temperature was raised to 70° C. and the reaction mixture was stirred for 20 h then poured onto an ice-cold aqueous saturated NaHCO3 solution and extracted with chloroform. The combined organic layer was concentrated and the light brown residue was purified on a silica gel column using chloroform/methanol/triethylamine, (50:10:1), as eluent to give 0.22 g (60% yield) of the title compound: 1H NMR (acetone-d6, 400 MHz) δ 8.47 (s, 1 H), 8.41 (s, H), 8.05 (d, J=8 Hz, 1 H), 7.99 (d, J=8 Hz, 1 H), 7.90 (d, J=8 Hz, 1 H), 7.19 (d, J=8 Hz, 1 H), 3.79 (br s, 2 H), 3.73 (br s, 4 H), 2.68 (br s, 4 H); MS (EI) m/z 369 (M+1+).

Workup

extractionextracted with chloroform
concentrationThe combined organic layer was concentrated
customthe light brown residue was purified on a silica gel column

Sources & evidence

ORD record: ord-e462217dadbf420983707bb58c4c11a3
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399780B2

Reaction notes

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