Sodium Hydroxide → 2-(1-(3-methoxy-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1515945Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:14]2[N:22](S(C3C=CC=CC=3)(=O)=O)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[CH:15]=2)=[CH:10][CH:11]([CH3:13])[CH3:12])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>C(O)C.O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:14]2[NH:22][C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[CH:15]=2)=[CH:10][CH:11]([CH3:13])[CH3:12])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 2-(1-(3-methoxy-phenyl)-3-methyl-but-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.87 g, 4.3 mmol) in ethanol (38.7 mL) and tetrahydrofuran (77.4 mL) was treated with an aqueous sodium hydroxide solution (10%, 14.6 mL). The reaction was stirred at 70° C. for 18 h. After cooling to 25° C., the reaction mixture was diluted with water (70 mL) and extracted with ethyl acetate (3×60 mL). The organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (30 g, petroleum ether/ethyl acetate 10:1) afforded 2-(1-(3-methoxy-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.05 g, 90%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ ppm 9.91 (s, 1H), 7.95 (dd, 1H, J1=3.6 Hz, J2=1.2 Hz), 7.89 (dd, 1H, J1=7.8 Hz, J2=1.2 Hz), 7.23 (t, 1H, J=7.8 Hz), 7.02 (s, 1H), 6.92-6.82 (m, 3H), 6.50 (s, 1H), 5.99 (d, 1H, J=9.9 Hz), 3.76 (s, 3H), 2.94-2.91 (m, 1H), 1.11 (s, 3H), 1.09 (s, 3H).

Workup

temperatureAfter cooling to 25° C.
extractionextracted with ethyl acetate (3×60 mL)
dry with materialThe organic extracts were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7405afc659c241f8b8e1fecc980e28cd
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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