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

HRID 215835Notes

Reaction equation

HRID 215835 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1842e03dcc3c4e88b8e9bd79e29eee2a
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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