Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | HCID 3837531 | HCID 3837531 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 73855097 | HCID 73855097 | 58.4% |
Reaction Steps
To a suspension of the product of Example 56 (1.06 g, 2 mmol) in DCM (10 mL) was added BBr3 (1.0 M in DCM, 2 mL) dropwise at −78° C. It was warmed to 20° C. slowly and the suspension was stirred for 72 h at 20° C. under N2. MeOH was added to decompose BBr3 at 0° C. Solvent was removed to give a crude, which was purified by chromatography on silica gel eluting with MeOH-DCM (2.5:97.5) to afford the title compound (0.6 g). 1H-NMR indicated one isomer. 1H-NMR (DMSO-d6): δ 9.66 (1H, s), 7.35 (1H, d), 7.13–7.24 (5H, m), 6.99 (1H, d), 6.60 (1H, d), 6.53 (1H, dd), 6.46 (1H, d), 4.96 (2H, s), 4.82(1H, t), 3.58 (3H, s), 2.89 (2H, m), 0.84 (3H, t); MS (ESI): 514 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07115640B2 |
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| Source dataset | uspto-grants-2006_10 |
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| ORD ID | ord-1d28f31f65cd4c1ba9dd34271efad945 |
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| Source note | uspto-grants-2006_10 |
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