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ノート

反応式

HRID 1792588 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-500e04ed0fc24c0e9e738faa257c8af8
出典データセット
uspto-grants-2006_07
特許番号
US07074801B1

反応ノート

読み込み中…