Ammonium Chloride → 3-[6-[tert-butylsilyloxy(diphenyl)methyl]-2-methylimidazo[1,2-a]pyridin-3-yl]-4-(1H-indol-3-yl)pyrrole-2,5-dione

HRID 216675

反応式

HRID 216675 の反応式
CC(C)([O-])C.[K+].CO[C:9](=[O:21])[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=O.[C:22]([SiH2:26][O:27][C:28]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:29]1[CH:30]=[CH:31][C:32]2[N:33]([C:35]([CH2:39][C:40]([NH2:42])=[O:41])=[C:36]([CH3:38])[N:37]=2)[CH:34]=1)([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>O1CCCC1.CCOC(C)=O>[C:22]([SiH2:26][O:27][C:28]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:29]1[CH:30]=[CH:31][C:32]2[N:33]([C:35]([C:39]3[C:40](=[O:41])[NH:42][C:9](=[O:21])[C:10]=3[C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][CH:13]=3)=[C:36]([CH3:38])[N:37]=2)[CH:34]=1)([CH3:25])([CH3:23])[CH3:24]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 588944Methyl 3-indoleglyoxylateHCID 23665647Potassium tert-butoxideHCID 1317297552-[6-(Tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyridin-3-yl]-acetamide

生成物 1

HCID 1317297543-[6-[tert-butylsilyloxy(diphenyl)methyl]-2-methylimidazo[1,2-a]pyridin-3-yl]-4-(1H-indol-3-yl)pyrrole-2,5-dione収率 47.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

Potassium tert-butoxide (1.0 M in THF, 1.90 ml, 1.90 mmol, 3.0 equiv) is added dropwise at room temperature under an atmosphere of argon to a solution of (1H-Indol-3-yl)-oxo-acetic acid methyl ester (192 mg, 0.93 mmol, 1.5 equiv) and of 2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyridin-3-yl]-acetamide (300 mg, 0.62 mmol) in anhydrous tetrahydrofuran (5.0 ml, dried over molecular sieves). The reaction mixture is stirred for 30 minutes at 0° C., 30 minutes at room temperature and 1 hour at 45° C. It is then diluted with EtOAc and poured into a saturated aqueous NH4Cl solution. After three extractions with EtOAc, the combined organic layers are dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue via flash chromatography (gradient of hexane/EtOAc 50:50 to 20:80) affords the title compound (180 mg, 45%). MS (ES+): 611 (M+H)+.

後処理

  1. extractionAfter three extractions with EtOAc
  2. dry with materialthe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue via flash chromatography (gradient of hexane/EtOAc 50:50 to 20:80)

出典と根拠

ORDレコード
ord-2597014dcd6e4282958a78e49cdc96fb
出典データセット
uspto-grants-2012_06
特許番号
US08193236B2

関連ノート

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