Triethylamine → HCID 22483982, compound

Temperature

80 °C

A 25 mL round bottom flask was charged with polymer bound 7-chloro-3-(piperidin-4-yl)-1H-indole (1.0 g, 0.98 mmol), triethylamine (80.2 mL), tert-butyl 3-bromopropionate and dry acetonitrile (5 mL). The mixture was stirred at 80° C. for 3 h. After cooling to room temperature, the resin was filtered off and washed with dry acetonitrile (3×10 mL) and dry dichloromethane (3×10 mL). The resin was treated for 20 minutes with 8 mL of a 1:1 mixture of dichloromethane and trifluoroacetic acid containing anisole (2%, w/w) and methionine (0.2%, w/w) (Caution: Generation of carbon dioxide). The resin was filtered off and washed with dry dichloromethane (10 mL), a 1:1 mixture of dichloromethane:triethylamine (3×10 mL) and dry dichloromethane (3×10 mL). The resin was dried in vacuo (20° C., 20 h) to yield the title resin (1.0 g).

1. additionA 25 mL round bottom flask was charged with polymer
2. temperatureAfter cooling to room temperature
3. filtrationthe resin was filtered off
4. washwashed with dry acetonitrile (3×10 mL) and dry dichloromethane (3×10 mL)
5. additionThe resin was treated for 20 minutes with 8 mL of a 1:1 mixture of dichloromethane and trifluoroacetic acid
6. additioncontaining anisole (2%, w/w) and methionine (0.2%, w/w) (Caution: Generation of carbon dioxide)
7. filtrationThe resin was filtered off
8. washwashed with dry dichloromethane (10 mL)
9. additiona 1:1 mixture of dichloromethane
10. customThe resin was dried in vacuo (20° C., 20 h)

ORD record

ord-9fc05cd01bd0487e9631ad6e99206de9

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07276508B2