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

HRID 44553

반응식

HRID 44553 반응식
[F:1][CH:2]([F:22])[C:3]1[NH:7][C:6]2[C:8]([C:18]([O:20][CH3:21])=[O:19])=[CH:9][C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:11][C:5]=2[N:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:32]=1[Cl:38]>CN(C=O)C>[Cl:38][C:32]1[C:33]([Cl:37])=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][N:4]1[C:5]2[CH:11]=[C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:9]=[C:8]([C:18]([O:20][CH3:21])=[O:19])[C:6]=2[N:7]=[C:3]1[CH:2]([F:1])[F:22]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27346021-(Bromomethyl)-2,3-dichlorobenzeneHCID 178498370HCID 178498370, 화합물

생성물 1

HCID 66976997methyl 1-(2,3-dichlorobenzyl)-2-(difluoromethyl)-6-morpholino-1H-benzo[d]imidazole-4-carboxylate수율 93%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

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]+

후처리

  1. customprepared
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. additionThe filtrate was poured into water (100 mL)
  5. filtrationfiltered
  6. customthe filter cake was collected
  7. custompurified by silica gel chromatography
  8. washeluted with petroleum ether

출처 및 근거

ORD 기록
ord-c22b564cad8a4b9782d07ad112a6b5ab
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541411B2

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