반응 #423153

반응 방정식

18-crown-6

potassium fluoride

(S)-2-fluoro-7-(2-fluoropyridin-3-yl)-3-iodo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine

trimethyl((3-methyloxetan-3-yl)ethynyl)silane

→

(S)-2-fluoro-7-(2-fluoropyridin-3-yl)-3-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine

수율 67.7%

용매

DMF

반응 조건

후처리

1. 1
   기타capped under argon
2. 2
   기타The reaction mixture was purified directly by column chromatography [0-100% (95:5 EtOAc/MeOH)/hexanes]

실험 절차

A vial charged with Pd(Ph3P)4 (0.035 g, 0.030 mmol), copper(I) iodide (5.80 mg, 0.030 mmol), 18-crown-6 (0.12 g, 0.46 mmol), potassium fluoride (0.035 g, 0.61 mmol), (S)-2-fluoro-7-(2-fluoropyridin-3-yl)-3-iodo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.15 g, 0.31 mmol, prepared as described in Method BB34), and trimethyl((3-methyloxetan-3-yl)ethynyl)silane (0.077 g, 0.46 mmol) was treated with 1.5 mL DMF, capped under argon, and was heated to 100° C. for 2 h. The reaction mixture was purified directly by column chromatography [0-100% (95:5 EtOAc/MeOH)/hexanes] yielding (S)-2-fluoro-7-(2-fluoropyridin-3-yl)-3-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.095 g, 0.206 mmol, 67.7% yield). MS m/z=461.0 [M+H]+. Calculated for C25H18F2N4O3: 460.43.

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