反応 #2286391

反応方程式

iodomethane

tert-butyl 2-(5-fluoropyridin-3-yl)-4-iodothiazol-5-ylcarbamate

sodium hydride

→

tert-butyl 2-(5-fluoropyridin-3-yl)-4-iodothiazol-5-yl(methyl)carbamate

収率 91.1%

溶媒

DMF

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction mixture was stirred at 0° C. for 30 min
2. 2
   その他The ice-water bath was removed
3. 3
   workup.STIRRINGthe mixture was stirred for an additional 1 hour
4. 4
   workup.ADDITIONdiluted with ethyl acetate (100 mL) and aqueous sodium bicarbonate (5 mL)
5. 5
   その他The organic phase was separated
6. 6
   洗浄rinsed with brine
7. 7
   乾燥dried over MgSO4
8. 8
   ろ過filtered
9. 9
   濃縮concentrated in vacuo
10. 10
    その他to give a yellow residue
11. 11
    その他This residue was purified on silica gel chromatography (6:4 hexane/ethyl acetate)

実験手順

To a solution of tert-butyl 2-(5-fluoropyridin-3-yl)-4-iodothiazol-5-ylcarbamate (1.20 g, 2.85 mmol) in DMF (5.7 mL) at 0° C. was added sodium hydride (125 mg, 3.13 mmol, 60% oil suspension) and the mixture was stirred at 0° C. for 10 min. To the yellow mixture was added iodomethane (0.49 g, 3.42 mmol) and the reaction mixture was stirred at 0° C. for 30 min. The ice-water bath was removed and the mixture was stirred for an additional 1 hour. The mixture was acidified with 0.1 N aq. HCl to neutral pH and diluted with ethyl acetate (100 mL) and aqueous sodium bicarbonate (5 mL). The organic phase was separated and rinsed with brine, dried over MgSO4, filtered and concentrated in vacuo to give a yellow residue. This residue was purified on silica gel chromatography (6:4 hexane/ethyl acetate) to give tert-butyl 2-(5-fluoropyridin-3-yl)-4-iodothiazol-5-yl(methyl)carbamate as a pale yellow solid (1.13 g, 91%): mp 70-71° C.; 1H NMR (300 MHz, CDCl3) δ 8.87 (s, 1H), 8.53 (bs, 1H), 7.99 (d, J=0.9 Hz, 1H), 3.23 (s, 3H), 1.45 (s, 9H); ESIMS m/z 436.1 (M+1).

出典