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Triphenylphosphine → 1-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-1,3-thiazol-2-yl)methoxy)pyridin-2(1H)-one

HRID 2203088
ノート
印刷プレビュー

反応式

HRID 2203088 の反応式
[CH2:1]([C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[C:10]([N:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]3=[O:20])[CH:11]=[CH:12][C:5]=2[N:4]=1)[CH3:2].[F:21][C:22]([F:31])([F:30])[C:23]1[N:24]=[C:25]([CH2:28]O)[S:26][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCCOC)=O)=NC(OCCOC)=O>C1COCC1.O>[CH2:1]([C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[C:10]([N:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:28][C:25]4[S:26][CH:27]=[C:23]([C:22]([F:31])([F:30])[F:21])[N:24]=4)=[CH:15][C:14]3=[O:20])[CH:11]=[CH:12][C:5]=2[N:4]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 23560688(4-(Trifluoromethyl)-1,3-thiazol-2-yl)methanolHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateHCID 896909981-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

生成物 1

HCID 896915391-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-1,3-thiazol-2-yl)methoxy)pyridin-2(1H)-one
収率 27.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(2-ethyl-1-methyl-1H-benzo[d]imidazol-6-yl)-4-hydroxypyridin-2(1H)-one (400 mg), (4-(trifluoromethyl)-1,3-thiazol-2-yl)methanol (544 mg) and triphenylphosphine (1.17 g) in THF (35 ml) was added bis(2-methoxyethyl) azodicarboxylate (1.04 g) at room temperature. After 3 h, the mixture was poured into water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/MeOH), followed by recrystallization from IPA-IPE to give the title compound (175 mg) as a white solid.

後処理

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/MeOH)
  6. customfollowed by recrystallization from IPA-IPE

出典と根拠

ORDレコード
ord-bab2c67d109b461097735990d57dd11f
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365540B2

反応ノート

読み込み中…

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