Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 86673084 | HCID 86673084 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Product | HCID 86673092 | HCID 86673092 | 72% |
Reaction Steps
In a 75 ml sealed tube were charged 6-bromo-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl-oxime (tert-butyl protected oxime of example 66) (250 mg, 0.60 mmol), palladium acetate (14 mg, 0.06 mmol), 1,1′-bis(diphenylphosphino)ferrocene (68 mg, 0.12 mmol), triethylamine (170 μl, 1.22 mmol), methanol (125 μl, 3.03 mmol) and dimethylformamide (5 ml). The suspension was degazed with carbone monoxide for 15 minutes. The tube was sealed and heated to 100° C. for 18 hours. The mixture was degazed with argon to remove the excess of carbone monoxide and then diluted with ethyl acetate, washed with a saturated solution of ammonium chloride, water, brine, dried over sodium sulfate and concentrated to dryness. The residue was purified by silica gel flash chromatography (gradient cyclohexane/ethyl acetate 0-80%) to yield the title compound as a yellow solid (172 mg, 72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962627B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-62c5eb5533a4413fbd57990c2682e7d1 |
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| Source note | uspto-grants-2015_02 |
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