Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Thiophene-3-boronic acid | HCID 581760 | — |
| Reactant | HCID 18796944 | HCID 18796944 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18796899 | HCID 18796899 | 88% |
Reaction Steps
A solution of the methyl 7-amino-2-chloro-thieno[2,3-b]pyrazine-6-carboxylate prepared as described in Example 10C (0.190 g), thiophene-3-boronic acid (0.100 g), Pd(dppf)C12 (0.032 g) and triethylamine (0.22 mL) in degassed DMF was heated to 95° C. for 4 h, cooled, quenched in water and extracted with 1:1 Et2O/EtOAc (3×). The organics were washed 3× with water, brine, dried (Na2SO4), filtered and solvent evaporated to give 0.200 g (88%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 3.95 (3H, s), 6.23 (2H, br s), 7.50 (1H, dd), 7.79 (1H, dd), 8.05 (1H, dd), 9.00 (1H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05891882 |
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| Source dataset | uspto-grants-1999_04 |
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| ORD ID | ord-58d337510bc64427a27b7554e622b579 |
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| Source note | uspto-grants-1999_04 |
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