반응 #72831

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1-(bromomethyl)-2,3-dichlorobenzene

methyl 2-(difluoromethyl)-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate

K2CO3

→

desired product

수율 93.0%

methyl 1-(2,3-dichlorobenzyl)-2-(difluoromethyl)-6-morpholino-1H-benzo[d]imidazole-4-carboxylate

수율 93.0%

용매

DMF

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후처리

1. 1
   기타prepared
2. 2
   온도The reaction mixture was cooled to room temperature
3. 3
   여과filtered
4. 4
   workup.ADDITIONThe filtrate was poured into water (100 mL)
5. 5
   여과filtered
6. 6
   기타the filter cake was collected
7. 7
   기타purified by silica gel chromatography
8. 8
   세척eluted with petroleum ether

실험 절차

A mixture of methyl 2-(difluoromethyl)-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate, prepared as described in Example 68 (1000 mg, 3.2 mmol), K2CO3 (884 mg, 6.4 mmol) and 1-(bromomethyl)-2,3-dichlorobenzene (926 mg, 3.8 mmol) in DMF (30 mL) was stirred at 70° C. for 18 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was poured into water (100 mL) and filtered, the filter cake was collected and purified by silica gel chromatography eluted with petroleum ether:EtOAc=1:1 to give the desired product (1.4 g, 93%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 3.16 (s, 4H), 3.74 (s, 4H), 3.92 (s, 3H), 5.77 (s, 2H), 6.21 (d, 1H, J=7.5 Hz), 7.20-7.58 (m, 5H); LC-MS: m/e=470 [M+1]+

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