Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Trimethylsilyl isocyanate | HCID 70696 | — |
| Reactant | HCID 67364015 | HCID 67364015 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67364123 | HCID 67364123 | — |
Reaction Steps
A solution of 3-[(S)-1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-(1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine (0.0030 g, 0.0077 mmol) in DCM (0.5 mL) was added a drop of TMS isocyanate. The reaction was stirred at 0° C. for 30 min. The solution was directly loaded onto Prep TLC (20×20 cm, silica gel, 5% MeOH in DCM) to afford the desired product. 1H-NMR (CD3OD, 400 MHz): δ=1.87 (d, J=7.1 Hz, 3 H), 2.22-2.44 (m, 2 H), 3.46-3.57 (m, 2H), 4.11-4.20 (m, 2 H), 5.27 (d, J=7.3 Hz, 1 H), 6.00 (t, J=2.0 Hz, 1 H), 7.11-7.24 (m, 1 H), 7.34 (dd, J=16.2, 1.8 Hz, 2 H), 8.19 (s, 1 H). MS (ES+): m/z 433.04/434.96 [MH+]. HPLC: tR=3.23 min (ZQ3, polar—5 min).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08592448B2 |
|---|
| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-cf4fe81b5a1f43f890f9ac8a832a4746 |
|---|
| Source note | uspto-grants-2013_11 |
|---|