HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → HCID 60205501, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bis(2-oxo-3-oxazolidinyl)phosphinic chloride | HCID 152842 | — |
| Reactant | Tetrahydro-2-furoic acid, (-)- | HCID 446666 | — |
| Reactant | 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine | HCID 60205276 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 60205501 | HCID 60205501 | 70.8% |
Reaction Steps
A mixture of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.869 mmol), (S)-tetrahydrofuran-2-carboxylic acid (252 mg, 2.17 mmol), triethylamine (606 μL, 4.35 mmol), and BOP—Cl (203 mg, 2.17 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 7 hours. 2M LiOH (5 mL) was added then to the mixture and stirred at room temperature for 30 minutes. Water (25 mL) was then added and stirred for an additional 30 minutes. The solid formed was filtered, washed with water (3×5 mL) and dried to provide (S)—N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)tetrahydrofuran-2-carboxamide (202 mg, 70.8% yield) as a solid. LCMS (APCI+) m/z 327.9, 329.9 (M+H)+; Retention time=2.80 minutes (Method 2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08545897B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-94da5aa159524104af29c8c293928b07 |
| Source note | uspto-grants-2013_10 |