Sodium Hydroxide → N,N-dimethyl-3-(3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)benzenamine

HRID 1515951Notes

Reaction equation

[CH3:1][N:2]([CH3:32])[C:3]1[CH:8]=[CH:7][CH:6]=[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:4]=1.[OH-].[Na+]>C(O)C.O1CCCC1.O>[CH3:32][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[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:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of N,N-dimethyl-3-(3-methyl-1-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl)but-1-enyl)benzenamine (3.0 g, 6.7 mmol) in ethanol (60 mL) and tetrahydrofuran (120 mL) was treated with an aqueous sodium hydroxide solution (10%, 23 mL). The reaction was stirred at 70° C. for 18 h. At this time, the reaction was cooled to 25° C., diluted with water (200 mL) and then extracted with ethyl acetate (2×100 mL). The organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (50 g, petroleum ether/ethyl acetate 10:1) afforded N,N-dimethyl-3-(3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)benzenamine (1.6 g, 76%) as a white solid: 1H NMR (300 MHz, CDCl3) δ ppm 8.46 (dd, 1H, J1=4.8 Hz, J2=1.8 Hz), 7.86 (dd, 1H, J1=7.8 Hz, J2=1.8 Hz), 7.65 (d, 2H, J=7.8 Hz), 7.37 (d, 1H, J=7.5 Hz), 7.24-7.15 (m, 2H), 6.51 (s, 1H), 6.13 (d, 1H, J=10.2 Hz), 2.78 (s, 6H), 2.71-2.64 (m, 1H), 1.28 (s, 3H), 1.25 (s, 3H).

Workup

temperatureAt this time, the reaction was cooled to 25° C.
extractionextracted with ethyl acetate (2×100 mL)
dry with materialThe organic extracts were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d1ed296233064a3b8a30d86cb579996e
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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