Nitrogen → 6-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine

HRID 1043996Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](I)[C:5]([NH2:9])=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:17][C:18]([CH3:22])([CH3:21])[C:19]#[CH:20].N#N>C1(C)C=CC=CC=1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[N:7]=[C:6]([C:20]#[C:19][C:18]([CH3:22])([CH3:21])[CH3:17])[C:5]([NH2:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 6-chloro-2-iodo-pyridin-3-ylamine (16.0 g, 62.7 mmol) in toluene (160 mL) and water (80 mL) were added Et3N (12.7 g, 125 mmol), Pd(PPh3)2Cl2 (2.2 g, 3.1 mmol), CuI (238 mg, 1.3 mmol) and 3,3-dimethyl-but-1-yne (7.7 g, 94 mmol) successively under N2 atmosphere. The reaction mixture was heated at 70° C. for 3 hours and was allowed to cool to room temperature. The resulting mixture was extracted with ethyl acetate (150 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give 6-chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine (11.5 g, 88%), which was used in the next step without further purification.

Workup

temperatureto cool to room temperature
extractionThe resulting mixture was extracted with ethyl acetate (150 mL×3)
dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
customevaporated under vacuum

Sources & evidence

ORD record: ord-1ce95d5be0f64daabb428b225b225bce
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563573B2

Reaction notes

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