Formic Acid → 1H-Pyrrolo(2,3-b)pyridine

HRID 603047Notes

Reaction equation

COCCOC[N:7]1[C:11]2=[N:12][CH:13]=[C:14](N3CCOCC3)[CH:15]=[C:10]2[C:9](C2C=CC=CC=2OC)=[CH:8]1.C(O)=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)C.O.[Cl-].[Na+].O>[NH:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH:9]=[CH:8]1

Participants

Conditions

Temperature: 65 °C

Procedure

65 mg (0.17 mmol) of 1-(2-methoxy-ethoxymethyl)-3-(2-methoxy-phenyl)-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridine was dissolved in a mixture of 3 ml of ethanol and 2 ml of water. 500 μl of formic acid was added and the mixture heated to 65° C. for 16 h and then irradiated in the microwave to 150° C. for 40 min. The resulting mixture was neutralized by addition of sodium bicarbonate and water and the crude distributed between ethyl acetate and brine. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated to afford 47 mg (0.15 mmol, 94% yield) of 3-(2-methoxy-phenyl)-5-morpholin-4-yl)-1H-pyrrolo[2,3-b]pyridine. 1H-NMR (d6-DMSO): δ11.58 (s, 1H), 8.11 (d, J=2.5 Hz, 1H), 7.59 (d, J=2.4 Hz, 1H), 7.51 (dd, J=1.4 Hz, 7.3 Hz, 1H), 7.46 (s, 1H), 7.27 (ddd, J=1.5 Hz, 8.8 Hz, 1H), 7.11 (d, J=8.3 Hz, 1H), 7.02 (dd(d), J=1.5 Hz, 7.3 Hz, 1H), 3.82 (s, 3H), 3.77 (m, 4H), 3.07 (m, 4H); MS: m/z 310 [MH+].

Workup

customirradiated in the microwave to 150° C. for 40 min
extractionThe aqueous phase was extracted twice with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-064b408f6384484b80ed49820ac7c2b1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906648B2

Reaction notes

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