Tributylphosphine → 4-[3-(2,6-Dichloro-phenyl-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-1H-indole-3-carboxylic acid methyl ester

HRID 250282Notes

Reaction equation

HRID 250282 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14]O)=[C:12]([CH:16]([CH3:18])[CH3:17])[O:11][N:10]=1.[CH3:19][O:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][C:28]([C:32]3[CH:37]=[CH:36][C:35](O)=[CH:34][C:33]=3[CH3:39])=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:22].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=[O:43].C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]([C:23]1[C:27]2[C:26](=[CH:31][CH:30]=[CH:29][C:28]=2[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:43][CH:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[C:13]3[CH:14]=[N:10][O:11][C:12]=3[CH:16]([CH3:18])[CH3:17])[C:33]=2[CH3:39])[NH:25][CH:24]=1)=[O:22]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanolHCID 57443273HCID 57443273, compound

Product 1

HCID 866254054-[3-(2,6-Dichloro-phenyl-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-1H-indole-3-carboxylic acid methyl esterYield 43.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of [3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-yl]-methanol (112 mg, 0.391 mmol) and 6-(4-hydroxy-2-methyl-phenyl)-1H-indole-3-carboxylic acid methyl ester (100 mg, 0.355 mmol) and toluene (7 mL) is added 1,1′-(azodicarbonyl)dipiperidine (99 mg, 0.39 mmol) followed by tri-n-butylphosphine (105 μL, 0.426 mmol). The mixture is allowed to stir overnight at room temperature. The reaction mixture is concentrated and purified via chromatography cluting with CH2Cl2 to give 85 mg (40%) of the title compound. ES/MS m/e 549.0 (M+1).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompurified via chromatography

Sources & evidence

ORD record
ord-95146fbc922b4a7ea608e918964be6e1
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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