Potassium Carbonate → Ethyl 7-(4-{6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]imidazo[1,2-a]pyridin-3-yl}phenoxy)heptanoate

HRID 1792588

반응식

HRID 1792588 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10]([C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:55]([O:57][CH2:58][CH3:59])=[O:56].I([O-])(=O)=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:27]=[CH:26][C:25]([O:28][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:55]([O:57][CH2:58][CH3:59])=[O:56])=[CH:24][CH:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10]([C:29]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:9]=2)=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 122490Ethyl 7-bromoheptanoateHCID 220313724-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenolHCID 23675764Sodium Iodate

생성물 1

HCID 22031256Ethyl 7-(4-{6-[3-(4-fluorophenyl)-1-trityl-1H-pyrazol-4-yl]imidazo[1,2-a]pyridin-3-yl}phenoxy)heptanoate수율 62.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of 200 mg 4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenol (compound in Example 14), 232 mg ethyl 7-bromoheptanoate, 6 mg sodium iodate, 68 mg potassium carbonate, and 15 mL N,N-dimethylformamide was stirred overnight at 80° C. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, then washed with water, an aqueous saturated sodium thiosulfate, an aqueous solution of sodium chloride (×2) and brine, and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 157 mg of the title compound as a pale brown amorphous.

후처리

  1. customthe organic layer was separated
  2. washwashed with water
  3. dry with materialan aqueous saturated sodium thiosulfate, an aqueous solution of sodium chloride (×2) and brine, and dried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. customThe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-500e04ed0fc24c0e9e738faa257c8af8
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074801B1

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