HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 3-(4-Formyl-2'-methyl-biphenyl-3-yloxy)-azetidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-Methylphenyl boronic acid | HCID 2733267 | — |
| Reactant | 3-(5-Bromo-2-formyl-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester | HCID 86657048 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Catalyst | Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene | HCID 129828017 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(4-Formyl-2'-methyl-biphenyl-3-yloxy)-azetidine-1-carboxylic acid tert-butyl ester | HCID 86657047 | 99.1% |
Reaction Steps
To 3-(5-Bromo-2-formyl-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (1.4 g, 3.9 mmol), 2-methylphenylboronic acid (0.55 g, 4.1 mmol), K3PO4 (2.5 g, 11.7 mmol), Pd(dba)2 (0.046 g, 0.080 mmol) and QPhos (0.114 g, 0.160 mmol) was added PhCH3 (16 mL). After 18 h at rt the reaction was diluted with EtOAc and filtered through a small silica pad. Silica gel chromatography (10-40% EtOAc in hexanes) gave 1.42 g (98% yield) of the title compound. 1H NMR (CDCl3): 7.26-7.18 (m, 4H), 6.94 (d, J=8.3 Hz, 1H), 6.90 (dd, J=8.2, 2.0 Hz, 1H), 6.55 (d, J=1.9 Hz, 1H), 4.90-4.86 (m, 1H), 4.26 (dd, J=10.1, 6.3 Hz, 2H), 4.12 (m, 4H), 2.26 (s, 3H), 1.49 (t, J=7.0 Hz, 3H), 1.44 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08575364B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-7459ccd20c89496783a416df7424fdf8 |
| Source note | uspto-grants-2013_11 |