Triethylamine → N-(2-morpholinoethyl)-5-(2-(trimethylsilyl)ethynyl)pyridin-2-amine

HRID 502679Notes

Reaction equation

I[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:6][CH:7]=1.[Si:17]([C:21]#[CH:22])([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>O1CCOCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[O:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][NH:8][C:5]2[CH:4]=[CH:3][C:2]([C:22]#[C:21][Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:7][N:6]=2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 80 °C

Procedure

5-Iodo-N-(2-morpholinoethyl)pyridin-2-amine (0.82 g, 2.46 mmol), TMS acetylene (1.70 mL, 12.3 mmol), and triethylamine (0.69 mL, 4.92 mmol) were dissolved in dioxane (20 mL) and with nitrogen for about 15 min. Tetrakis(triphenylphosphine)palladium (142 mg, 0.12 mmol) and copper (I) iodide (47 mg, 0.25 mmol) were added before the reaction mixture was heated to 80° C. for 3.5 h. The reaction mixture was diluted with 100 mL EtOAc, washed with 50 mL saturated, aqueous NaHCO3, and dried over anhydrous Na2SO4. After purification by chromatography, the title compound was obtained. MS (ES+): 304 (M+H)+.

Workup

washwashed with 50 mL saturated
dry with materialaqueous NaHCO3, and dried over anhydrous Na2SO4
customAfter purification by chromatography

Sources & evidence

ORD record: ord-b99b9972a5b04940954d2d59d62ef4c5
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776869B2

Reaction notes

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