반응 #67031

반응 방정식

4-Bromo-2-fluorobenzamide

aminoisobutyric acid

K2CO3

2-acetyl cyclohexanone

→

2-(4-carbamoyl-3-fluorophenylamino)-2-methylpropanoic acid

용매

H2O

DMF

H2O

반응 조건

후처리

1. 1
   세척the aqueous layer was washed with ethyl acetate (20 mL)
2. 2
   추출the product was extracted with ethyl acetate (20 mL×3)
3. 3
   건조The combined organic layer was dried over anhydrous Na2SO4
4. 4
   농축concentrated under reduced pressure
5. 5
   기타to obtain the product

실험 절차

4-Bromo-2-fluorobenzamide (0.5 g, 2.29 mmol), 2 aminoisobutyric acid (0.354 g, 3.54 mmol), CuI (87 mg, 0.458 mmol), and K2CO3 (0.790 g, 5.72 mmol) were mixed in DMF (5 mL). H2O (0.5 mL) and TEA (11 mg, 0.1 mmol) were added followed by 2-acetyl cyclohexanone (60 mg, 0.428 mmol).The reaction mixture was heated to 95-100° C. for 48 h. The reaction mixture was diluted with H2O (20 mL) and the aqueous layer was washed with ethyl acetate (20 mL). The aqueous layer was acidified with 1M citric acid to pH 4 and the product was extracted with ethyl acetate (20 mL×3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the product. 1H NMR (DMSO, Freebase): δ (ppm) 7.55-7.45 (t, 1H), 7.20 (bs, 1H), 7.05 (bs, 1H), 6.80 (bs, 1H), 6.35-6.30 (d, 1H), 6.18-6.10 (d, 1H), 1.42 (s, 6H).

출처