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

HRID 215835
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HRID 215835 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-1842e03dcc3c4e88b8e9bd79e29eee2a
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193192B2

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