Tetrahydrofuran → 2-amino-3-fluoro-N-prop-2-ynyl-benzamide

반응식

[F:1][C:2]1[C:7]2[NH:8]C(=O)O[C:11](=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.O1CCCC1.[CH2:19]([NH2:22])[C:20]#[CH:21]>>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=1[C:11]([NH:22][CH2:19][C:20]#[CH:21])=[O:12]

참가 물질

반응물 3

HCID 8028Tetrahydrofuran

HCID 239041Propargylamine

HCID 105353938-Fluoroisatoic anhydride

생성물 1

HCID 815106892-amino-3-fluoro-N-prop-2-ynyl-benzamide수율 79%

실험 절차

8-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (3.00 g, 16.6 mmol) was dissolved in tetrahydrofuran (100 mL, 1.23 mol) and prop-2-ynylamine (1.70 mL, 24.8 mmol) was added. The reaction was stirred for 2 hours and then concentrated under reduced pressure onto silica gel. Purification by silica gel chromatography (dry loaded) using a gradient of 0-60% EtOAc/hex as the eluting solvent to obtain 2-amino-3-fluoro-N-prop-2-ynyl-benzamide as a white solid (2.52 g, 79%). m.p.=89-91° C.; LCMS (m/e) 138 (M—NHCH2CCH); 1H-NMR (CDCl3, 400 MHz) δ 7.14 (d, 1H, J=8.0 Hz), 7.12-7.05 (m, 1H), 6.64-6.56 (m, 1H), 6.28-6.14 (m, 1H), 5.67 (bs, 2H), 4.27-4.19 (m, 2H), 2.34-2.27 (m, 1H).