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

HRID 250293Notes

Reaction equation

HRID 250293 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]([OH:38])=[CH:34][C:33]=3C)=[CH:29][CH:30]=2)[N:25]([CH:40]([CH3:42])[CH3:41])[C:24]=1[CH3:43])=[O:22].[CH2:44](P(CCCC)CCCC)CCC.C1CCN([C:63](/N=N/C(N2CCCCC2)=O)=[O:64])CC1>C1(C)C=CC=CC=1.CCCCCC>[CH2:19]([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:38][CH2:14][C:13]4[C:9]([C:3]5[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=5[Cl:8])=[N:10][O:11][C:12]=4[CH:16]([CH3:18])[CH3:17])=[CH:34][C:33]=3[O:64][CH3:63])=[CH:29][CH:30]=2)[N:25]([CH:40]([CH3:42])[CH3:41])[C:24]=1[CH3:43])=[O:22])[CH3:44]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanolHCID 672718996-(4-Hydroxy-2-methyl-phenyl)-1-isopropyl-2-methyl-1H-indole-3-carboxylic acid methyl ester

Product 1

HCID 672721076-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-methoxy-phenyl}-1-isopropyl-2-methyl-1h-indole-3-carboxylic acid ethyl esterYield 34.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-yl]-methanol (0.2 g, 0.71 mmol), 1-isopropyl-6-(4-hydroxy-2-methyl-phenyl)-2-methyl-1H-indole-3-carboxylic acid methyl ester (0.2 g, 0.59 mmol), tri-n-butylphosphine (0.14 g, 0.71 mmol) and azodicarboxylic acid dipiperidide (0.18 g, 0.71 mmol) are stirred in dry toluene (9 mL) for 2 days at room temperature. The reaction is diluted with hexane (9 mL), stirred for 30 minutes, and filtered. The filtrate is concentrated and the residue purified via flash chromatography (40 g SiO2) eluting with 30% THF in heptane to afford the title compound (124 mg, 34.6%). ES/MS m/e 606.8 (M+1)

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated
  3. customthe residue purified via flash chromatography (40 g SiO2)
  4. washeluting with 30% THF in heptane

Sources & evidence

ORD record
ord-bf57e2da9e2b411e8b2b962dec9d222d
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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