Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| Reactant | HCID 24874900 | HCID 24874900 | — |
| Product | HCID 59596278 | HCID 59596278 | 93% |
Reaction Steps
To [3-(6-hydroxy-3′-methoxy-biphenyl-3-yl)-3-(4-methoxy-phenyl)-3H-isoindol-1-yl]-carbamic acid tert-butyl ester (Scheme #2, F) (196 mg, 0.365 mmol) in an ice cold solution of dichloromethane was added pyridine (60.0 uL, 0.730 mmol) followed by trifluoromethanesulfonic anhydride (93 uL, 0.438 mmol). After stirring for 30 minutes the reaction was removed of solvent under reduced pressure and the crude mixture was purified on 20 g silica eluting with 5% acetone/dichloromethane to give the title compounds as a white solid (226 mg, 93%). 1H NMR (300 MHz, DMSO-d6) δ 7.86 (d, J=7.5 Hz, 1 H), 7.72-7.64 (m, 2 H), 7.58-7.36 (m, 5 H), 7.28-7.20 (m, 2 H), 7.02-6.84 (m, 5 H), 3.77 (s, 3 H), 3.72 (m, 3 H), 1.49 (m, 9 H); MS (APCI+) m/z 669 [M+1]+; tR=2.94 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07855213B2 |
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| Source dataset | uspto-grants-2010_12 |
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| ORD ID | ord-62dcddcbd0ca44f9b22340a7c3226e32 |
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| Source note | uspto-grants-2010_12 |
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