Dimethyl Sulfoxide → 1-(4'-{5-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-1-methyl-1H-pyrazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

HRID 919092Notes

Reaction equation

HRID 919092 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[N:23][N:24]([CH3:30])[C:25]=4[CH:26]([OH:29])[C:27]#[CH:28])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:31]([N:38]=[N+:39]=[N-:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CS(C)=O.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2].CCOC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[N:23][N:24]([CH3:30])[C:25]=4[CH:26]([C:27]4[N:40]=[N:39][N:38]([CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[CH:28]=4)[OH:29])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 866970911-{4'-[5-(1-Hydroxy-prop-2-ynyl)-1-methyl-1H-pyrazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 679596491-(4'-{5-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-1-methyl-1H-pyrazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 22728543Water ethylacetateSolvent

Procedure

1-{4′-[5-(1-Hydroxy-prop-2-ynyl)-1-methyl-1H-pyrazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.17 g, 0.45 mmol) and benzyl azide (0.072 g, 0.54 mmol) were combined DMSO (5 mL). Copper(II) sulfate (0.001 g, 0.005 mmol) and sodium ascorbate (0.001 g, 0.05 mmol) were combined in H2O (2 mL) and the solution was added to the DMSO mixture. The reaction was stirred at room temperature for 18 hours then submitted to EtOAc/H2O workup. Purification on silica gel (0-70% EtOAc in hexanes) provided the title compound.

Workup

  1. customPurification on silica gel (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b503df4c22b2428b84c04444e54d3af1
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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