Cesium carbonate → Tert-butyl (4-((2-chloropyridin-4-yl)methoxy)naphthalen-1-yl)carbamate

Temperatur

55 °C

To a mixture of 2-chloro-4-(chloromethyl)pyridine (30 g, 185 mmol) and tert-butyl (4-hydroxynaphthalen-1-yl)carbamate (40.0 g, 154 mmol) in acetonitrile (200 mL) was added caesium carbonate (75 g, 231 mmol) and the resulting mixture was heated to 55° C. After 16 h the reaction mixture was diluted with 30% MeOH in DCM (600 mL) and water (400 mL). The layers were separated and the aqueous layer was extracted with a further amount of 30% MeOH in DCM (2×600 mL) and the organics were concentrated in vacuo to afford the crude product. The crude product was triturated with MeOH (200 mL), sonicated for c.a. 5 min and slurried for 1 day. The resulting solid was collected by filtration and washed with MeOH (2×10 mL) to yield the subtitle compound tert-butyl (4-((2-chloropyridin-4-yl)methoxy)naphthalen-1-yl)carbamate as a yellow solid (43 g, 70%); Rt 2.60 min (Method 1); m/z 383 (M−H)− (ES−); 1H NMR δ:1.47 (9H, s), 5.41 (2H, s), 6.98 (1H, d), 7.36 (1H, d), 7.55-7.61 (3H, overlapping m), 7.65 (1H, m), 7.94 (1H, m), 8.29 (1H, m), 8.45 (1H, m), 9.00 (1H, bs).

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with a further amount of 30% MeOH in DCM (2×600 mL)
3. concentrationthe organics were concentrated in vacuo
4. customto afford the crude product
5. customThe crude product was triturated with MeOH (200 mL)
6. customsonicated for c.a
7. filtrationThe resulting solid was collected by filtration
8. washwashed with MeOH (2×10 mL)

ORD-Eintrag

ord-e1afda266d91492abcd43fe9d301669f

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09447076B2