Triethylamine → HCID 22452629, compound

To a stirred, cooled (0° C.) suspension of 4-iodo-3-methoxy-5,6,7,8-tetrahydro-2-naphthalenecarboxamide (2.06 g, 6.22 mmol), triethylamine (2.77 mL, 19.91 mmol), and THF (40 mL) was added trifluoroacetic anhydride (1.23 mL, 8.71 mmol) dropwise via syringe. After addition, the ice bath was removed and the reaction stirred overnight at ambient temperature. The mixture was cooled to 0° C. and excess trifluoroacetic anhydride destroyed with H2O (2 mL). Ethyl acetate (50 mL) was added and the organic layer was washed with H2O (3×25 mL) and brine (25 mL), dried (NaSO4), filtered, concentrated in vacuo and purified by chromatography (100% DCM) to afford a light brown solid (1.96 g, 100%). 1H NMR (CDCl3) δ 7.29 (s, 1H), 4.0 (s, 3H), 2.74 (m, 4H), 1.76 (m, 4H), MS m/z 314 (M+H).

1. temperatureTo a stirred, cooled
2. additionAfter addition
3. customthe ice bath was removed
4. temperatureThe mixture was cooled to 0° C.
5. customexcess trifluoroacetic anhydride destroyed with H2O (2 mL)
6. additionEthyl acetate (50 mL) was added
7. washthe organic layer was washed with H2O (3×25 mL) and brine (25 mL)
8. dry with materialdried (NaSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. custompurified by chromatography (100% DCM)

ORD record

ord-2f04be89c25841d884870ddf74d9735d

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06403601B1