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Triphenylphosphine → Methyl 4-(5-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)-3-methylpyridin-2-yloxy)benzoate

HRID 215835
ノート
印刷プレビュー

反応式

HRID 215835 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]([O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[C:28]1[C:32]([CH2:33]O)=[C:31]([CH:35]([CH3:37])[CH3:36])[O:30][N:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1C=CC=CC=1>[Cl:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[C:22]=1[C:28]1[C:32]([CH2:33][O:1][C:2]2[CH:3]=[C:4]([CH3:19])[C:5]([O:8][C:9]3[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=3)=[N:6][CH:7]=2)=[C:31]([CH:35]([CH3:37])[CH3:36])[O:30][N:29]=1
参加物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 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanolHCID 67297146Methyl 4-(5-hydroxy-3-methylpyridin-2-yloxy)benzoate

生成物 1

HCID 67297286Methyl 4-(5-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)-3-methylpyridin-2-yloxy)benzoate収率 70.2%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a suspension of methyl 4-(5-hydroxy-3-methylpyridin-2-yloxy)benzoate synthesised in step 3 (0.042 g, 0.162 mmol), [3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-yl]methanol (0.046 g; 0.162 mmol) (for preparation refer to: P. Maloney et al. “Identification of a chemical tool for the orphan nuclear receptor FXR” J. Med. Chem. 2000, 43(16), 2971-2974) and triphenylphosphine (0.052 g, 0.2 mmol) in benzene (2 ml) was added diisopropyl azodicarboxylate (0.051 g, 0.25 mmol). The mixture was stirred at room temperature for 20 h, the solvent was removed in vacuo and the residue was purified by preparative HPLC to provide methyl 4-(5-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)-3-methylpyridin-2-yloxy)benzoate (0.06 g, 70% yield).

後処理

  1. customfor preparation
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-1842e03dcc3c4e88b8e9bd79e29eee2a
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08193192B2

反応ノート

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