HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 86707737, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Ethyl 3-chloro-3-oxopropionate | HCID 118931 | — |
| Reactant | 4-Bromo-2,6-difluoroaniline | HCID 610191 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86707737 | HCID 86707737 | 65% |
Reaction Steps
To a solution of 4-bromo-2,6-difluoroaniline (10 g, 48 mmol) in DCM (15 mL) was added ethyl 3-chloro-3-oxopropanoate (6.8 mL, 53 mmol) and DIEA (9.2 mL, 53 mmol) at room temperature. After 1 hour, the reaction mixture was partitioned between H2O and DCM. The organic phase was washed with saturated NH4Cl, H2O, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to give Compound B26a (10 g, 65% yield). HPLC: RT=1.6 (LCMS Method Q). MS (ES): m/z=321.9 [M+H]+. 1H NMR (500 MHz, CHLOROFORM-d) δ 8.89 (br. s., 1H), 7.20-7.15 (m, 2H), 4.29 (q, J=7.2 Hz, 2H), 3.54 (s, 2H), 1.36-1.31 (m, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987314B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-c6b6f445591a4609b16622a3a40ab19f |
| Source note | uspto-grants-2015_03 |