HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 335831Generated: October 30, 2026
Diisopropylamine → (S)-4-(2-amino-5'-fluoro-2'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)-2-methylbut-3-yn-2-ol
https://huagongshe.com/reaction/335831
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | 2-Methyl-3-butyn-2-ol | HCID 8258 | — |
| Reactant | (S)-2-amino-5'-fluoro-2'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl trifluoromethanesulfonate | HCID 86640722 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-4-(2-amino-5'-fluoro-2'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)-2-methylbut-3-yn-2-ol | HCID 67383734 | — |
Reaction Steps
A 15 ml resealable tube was charged with (S)-2-amino-5′-fluoro-2′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl trifluoromethanesulfonate (300 mg, 0.584 mmol), tetrakis(triphenylphosphine)palladium(0) (67.5 mg, 0.058 mmol), copper(i) iodide (11.13 mg, 0.058 mmol), DMF (2922 μL), 2-methylbut-3-yn-2-ol (114 μL, 1.169 mmol) and diisopropylamine (416 μL, 2.92 mmol). The mixture was capped with argon, sealed and heated at 85° C. for 1 hr. Concentration and purification of the crude residue by silica gel chromatography (10-60% CH2Cl2/MeOH/NH4OH 90:10:1 in CH2Cl2) afforded (S)-4-(2-amino-5′-fluoro-2′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)-2-methylbut-3-yn-2-ol. MS m/z=448.0 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08883782B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-aaa3eda660c6484996800a2459d40c52 |
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| Source note | uspto-grants-2014_11 |
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