Dimethylamine → 5-Chloro-3-(2-(6-ethynylpyridin-2-yl)-2-oxoethyl)-3-hydroxy-1-propylindolin-2-one

HRID 1523059Notes

Reaction equation

C[Si]([C:5]#[C:6][C:7]1[N:12]=[C:11]([C:13](=[O:15])[CH3:14])[CH:10]=[CH:9][CH:8]=1)(C)C.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][CH2:27][CH3:28])[C:21](=[O:29])[C:20]2=[O:30].CNC>CO>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][CH2:27][CH3:28])[C:21](=[O:29])[C:20]2([CH2:14][C:13]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([C:6]#[CH:5])[N:12]=1)=[O:15])[OH:30]

Participants

Conditions

Temperature: 80 °C

Procedure

To a clean biotage vial equipped with a stir bar was added 1-(6-((trimethylsilyl)ethynyl)pyridin-2-yl)ethanone (0.0255 grams, 0.12 mmol), 5-chloro-1-propylindoline-2,3-dione, (0.015 grams, 0.067 mmol). This was taken up in 0.2 mL of methanol (purchased from Fisher Scientific). Dimethylamine (2.5 μL 40% in water purchased from Fisher Scientific) was then added and the solution heated in a Biotage initiator microwave for ten minutes at 80° C. Once complete, the reaction was concentrated using a Buchi rotoevaporator and purified using a Teledyne ISCO with silica gel (hexane, ethyl acetate gradient). Yield, 40%. 1H-NMR δ 8.06 (dd, 1H), 7.89 (t, 1H), 7.69 (dd, 1H), 7.35 (d, 1H), 7.29 (dd, 1H), 6.80 (d, 1H), 6.02 (s, 1H), 3.88 (d, 1H), 3.62 (m, 3H), 3.25 (s, 1H), 1.71 (m, 2H), (0.97 (t, 3H). calculated mass for C20H17ClN2O3, 368.09. Observed, 369.0 (M+1).

Workup

customTo a clean biotage vial equipped with a stir bar
concentrationOnce complete, the reaction was concentrated
custompurified
customYield

Sources & evidence

ORD record: ord-a151760c388a4bef9e4aa55bddcf01b5
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079853B2

Reaction notes

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