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

HRID 1515942Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]([C:15]2[N:23](S(C3C=CC=CC=3)(=O)=O)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[CH:16]=2)=[CH:11][CH:12]([CH3:14])[CH3:13])[CH:7]=[CH:8][CH:9]=1)[CH3:2].[OH-].[Na+]>C(O)C.O1CCCC1.O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]([C:15]2[NH:23][C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[CH:16]=2)=[CH:11][CH:12]([CH3:14])[CH3:13])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 2-(1-(3-ethoxy-phenyl)-3-methyl-but-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (2.2 g, 4.9 mmol) in ethanol (58.5 mL) and tetrahydrofuran (117 mL) was treated with an aqueous sodium hydroxide solution (10%, 22 mL). The reaction was stirred at 70° C. for 18 h. After cooling to 25° C., the reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (2×150 mL). The organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (50 g, ethyl acetate/petroleum ether 1:15) afforded 2-(1-(3-ethoxy-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.3 g, 86%) as a yellow oil: 1H NMR (300 MHz, d6-DMSO) δ ppm 11.59 (s, 1H), 8.16 (d, 1H, J=4.5 Hz), 7.92 (d, 1H, J=7.5 Hz), 7.19 (t, 1H, J=7.8 Hz), 7.04 (q, 1H), 6.82 (t, 2H, J=2.1 Hz), 6.72 (s, 1H), 6.36 (d, 1H, J=1.8 Hz), 6.15 (d, 1H, J=9.9 Hz), 3.95 (q, 2H, J=13.8 Hz), 2.61-2.49 (m, 1H), 1.26 (t, 3H, J=6.9 Hz), 1.03 (s, 3H), 1.01 (s, 3H).

Workup

temperatureAfter cooling to 25° C.
extractionextracted with ethyl acetate (2×150 mL)
dry with materialThe organic extracts were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fc4e8316cd91437fb564aa622e26adc2
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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