Tributylphosphine → 4-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-benzylamino}-benzoic acid methyl ester

HRID 424835Notes

Reaction equation

HRID 424835 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[N:10]1.[CH3:19][O:20][C:21](=[O:38])[C:22]1[CH:27]=[CH:26][C:25]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33](O)=[CH:32][C:31]=2[CH3:37])=[CH:24][CH:23]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCCC>[CH3:19][O:20][C:21](=[O:38])[C:22]1[CH:23]=[CH:24][C:25]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:15][CH2:14][C:13]3[N:9]([C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[N:10]=[N:11][C:12]=3[CH:16]([CH3:18])[CH3:17])=[CH:32][C:31]=2[CH3:37])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 45790389(1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanolHCID 667042034-(4-Hydroxy-2-methyl-benzylamino)-benzoic acid methyl ester

Product 1

HCID 667041474-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-benzylamino}-benzoic acid methyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

To a 0° C. solution of [3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-yl]-methanol (309 mg, 1.08 mmol), 4-(4-hydroxy-2-methyl-benzylamino)-benzoic acid methyl ester (292 mg, 1.08 mmol), and tri-n-butylphosphine (344 mg, 1.70 mmol) in toluene (50 mL) is added 1,1′-(Azodicarbonyl)-dipiperidine (450 mg, 1.78 mmol). The reaction mixture is stirred for 1.5 h. The reaction mixture is diluted with heptane, filtered, and concentrated under reduced pressure. The residue is purified by flash chromatography (40 g silica, gradient EtOAc/Hexane) to give 4-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-benzylamino}-benzoic acid methyl ester (309 mg, 1.08 mmol). MS: 539.0 (M+1).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by flash chromatography (40 g silica, gradient EtOAc/Hexane)

Sources & evidence

ORD record
ord-41501f0d515547a49807d2df6a2d47d4
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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