Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Benzophenone imine | HCID 136809 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Methyl 5-bromo-1,3-thiazole-4-carboxylate | HCID 40787018 | — |
| Catalyst | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86649429 | HCID 86649429 | 84.4% |
Reaction Steps
A mixture of methyl 5-bromothiazole-4-carboxylate (3.51 g, 15.8 mmol), diphenylmethanimine (4.0 ml, 23.9 mmol), cesium carbonate (10.98 g, 33.7 mmol), Pd2(dba)3-CHCl3 (876 mg, 957 umol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 1.67 g, 2.89 mmol) in toluene (30 ml) was heated at 80° C. for 18 h. The heterogeneous mixture was directly flash chromatographed with 9:1, 4:1, 7:3, 3:2 and 1:1 hexane:ethyl acetate as the eluant to yield 4.30 g (84% yield) of methyl 5-(diphenylmethyleneamino)thiazole-4-carboxylate as a yellow oil. Retention time (min)=6.41, method [7], MS(ESI) 323.0 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09073891B2 |
|---|
| Source dataset | uspto-grants-2015_07 |
|---|
| ORD ID | ord-96faa2e9891c44cc93d9c0f39ba7a98e |
|---|
| Source note | uspto-grants-2015_07 |
|---|
