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2-Bromopyridine → HCID 178479691、化合物

HRID 2233788
ノート
印刷プレビュー

反応式

HRID 2233788 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]1=[C:22]([C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)=[O:34])[C:23]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=[O:29])=[O:24].[Cl-:42].[NH4+]>C1COCC1>[ClH:42].[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]1=[C:22]([C:23]([C:25]1[CH:32]=[CH:31][CH:30]=[C:27]([CH:28]([OH:29])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:26]=1)=[O:24])[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)=[O:34]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 79732-BromopyridineHCID 25517Ammonium ChlorideHCID 178418339ButyllithiumHCID 178519574HCID 178519574、化合物

生成物 1

HCID 178479691HCID 178479691、化合物収率 42%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

0.33 ml portion of 2-bromopyridine was dissolved in 3 ml of THF, and the solution was cooled to −78° C., mixed with 2.2 ml of n-butyl lithium and then stirred at the same temperature for 30 minutes. This solution was poured at −78° C. into a solution prepared by dissolving 3-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]benzaldehyde in 10 ml of THF. This was slowly risen to room temperature and mixed with 50 ml of saturated ammonium chloride aqueous solution. This was extracted with ethyl acetate, dried with sodium sulfate and then concentrated, and the thus formed residue was purified by a silica gel column chromatography (chloroform:methanol=from 100:0 to 90:10). By subjecting the thus obtained reddish brown solid to salt formation with 4N HCl/EtOAC (0.2 ml), 151 mg (42%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-{3-[hydroxy(pyridin-2-yl)methyl]phenyl}propane-1,3-dione hydrochloride (Example 11-1) was obtained. FA: 466

後処理

  1. additionThis solution was poured at −78° C. into a solution
  2. customprepared
  3. customThis was slowly risen to room temperature
  4. extractionThis was extracted with ethyl acetate
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customthe thus formed residue was purified by a silica gel column chromatography (chloroform:methanol=from 100:0 to 90:10)

出典と根拠

ORDレコード
ord-d4fbc71ea09f4695a1e4125f852e8cfc
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07709519B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート