HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 595960Generated: October 29, 2026
Dichloromethane → tert-butyl 4-(3-amino-6-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yl)-2-fluorobenzoate
https://huagongshe.com/reaction/595960
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 10932675 | — |
| Reactant | tert-Butyl 4-(3-amino-6-bromopyrazin-2-yl)-2-fluorobenzoate | HCID 118045500 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | tert-butyl 4-(3-amino-6-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yl)-2-fluorobenzoate | HCID 118045381 | 85% |
Reaction Steps
To a solution of tert-butyl 4-(3-amino-6-bromopyrazin-2-yl)-2-fluorobenzoate (21 g, 57.0 mmol) in DME (127 mL) was added PdCl2(dppf).CH2Cl2 adduct (2.329 g, 2.85 mmol), 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.18 g, 62.7 mmol), and 2 M Na2CO3aqueous solution (63.4 mL). The reaction was heated at 110° C. for 16 h. To the reaction mixture was added 200 mL of ethyl acetate, washed with water (2×100 mL), brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography eluting with 0-100% of EtOAc/DCM to provide tert-butyl 4-(3-amino-6-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yl)-2-fluorobenzoate (18 g, 48.5 mmol, 85%). LCMS (m/z): 372.3 (MH+), 0.95 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09242996B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-73336f647bac4e2b8ed8284c66731fb4 |
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| Source note | uspto-grants-2016_01 |
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