HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | diazenedicarboxylic acid bis(N,N-piperidide) | HCID 5702657 | — |
| Reactant | (3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanol | HCID 10850745 | — |
| Reactant | 6-(4-Hydroxy-2-methyl-phenyl)-1-isopropyl-2-methyl-1H-indole-3-carboxylic acid methyl ester | HCID 67271899 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 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 | HCID 67272107 | 34.6% |
Reaction Steps
[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)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07863302B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-bf57e2da9e2b411e8b2b962dec9d222d |
| Source note | uspto-grants-2011_01 |