1,7-DIFLUORO-6-METHOXYISOQUINOLINE synthesis

5synthesis methods

Product Name:1,7-DIFLUORO-6-METHOXYISOQUINOLINE
CAS Number:1409964-64-2
Molecular formula:C10H7F2NO
Molecular Weight:195.17

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Yield:1409964-64-2 68%

Reaction Conditions:

with cesium fluoride in dimethyl sulfoxide at 145; for 18 h;Sealed tube;

Steps:

5 Step 5: Preparation of1 ,7-difluoro-6-methoxyisoquinoline

Step 5: Preparation of1 ,7-difluoro-6-methoxyisoquinoline 10164] To a solution of 1-chloro-7-fluoro-6-methoxyiso- quinoline (1.5 g, 7.09 mmol) in DMSO was added cesium fluoride (2.15 g, 14.18 mmol) at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 145° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2504 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (950 mg, 68%) as white solid. ‘H NMR (400 MHz, CDC13): ? ppm 8.0-7.98 (m, 1H), 7.77-7.74 (d, J=12 Hz, 1H), 7.42-7.40 (m, 1H), 7.21-7.19 (m, 1H), 4.04 (s, 3H); ‘9F NMR:? ppm -129.05 (1 F), -71.98 (iF); MS: MS mlz 196.1 (M+1).

References:

US2015/284409,2015,A1 Location in patent:Paragraph 0159; 0164

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