Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | {(S)-6-[(R)-4-bromo-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester | HCID 86697103 | — |
| Reactant | HCID 178478124 | HCID 178478124 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86700787 | HCID 86700787 | — |
Reaction Steps
The title compound is prepared from {(S)-6-[(R)-4-bromo-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (84 mg), (2-chloro-pyrid-5-yl)methylzinc chloride (0.5 moL/L in tetrahydrofuran, 1.2 mL) and tetrakis(triphenylphosphine)palladium (23 mg). Degassed tetrahydrofuran (1 mL) is added under Ar atmosphere, and the mixture is heated to 60° C. and shaken at this temperature overnight. The mixture is acidified with 4 N aqueous hydrochloric acid (1 mL) and then neutralized with saturated aqueous ammonia solution. The organic phase is separated, diluted with N,N-dimethylformamide (1 mL), and purified by HPLC on reversed phase (MeCN/water) to give the title compound. LC (method 6): tR=1.04 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809376B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-c7b62cb8ca284d859f4101c58cfa74b6 |
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| Source note | uspto-grants-2014_08 |
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