Water → 1-(6-Fluoro-3-methyl-1H-indazol-1-yl)ethanone

HRID 1377510Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:11])=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].CCN(C(C)C)C(C)C.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:12]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=2)[C:6]([CH3:11])=[N:7]1)(=[O:14])[CH3:13]

Participants

Conditions

Temperature: 20 °C

Procedure

6-Fluoro-3-methyl-1H-indazole (2.79 g, 18.6 mmol) in CH2Cl2 (50 mL) was treated with acetic anhydride (2.8 g, 30 mmol), Hunig's base (5.2 mL, 30 mmol) and DMAP (0.2 g, 1.7 mmol). The mixture was stirred 1 h at 20° C., poured into water (100 mL) and extracted with CH2Cl2 (2×100 mL). The extracts were dried (Na2SO4), concentrated and the residue recrystallised from hexane to give the title compound (3.41 g, 96%) as a white crystalline solid; mp 89°-91° C. (from hexane); 1H NMR (360 MHz, CDCl3) δ 8.05 (dd, J=9.4, 2.2 Hz, 1H, indazole), 7.51 (dd, J=8.7, 5.1 Hz, 1H, indazole), 7.03 (dt, J=8.8, 2.2 Hz, 1H, indazole), 2.67 (s, 3H, Me), 2.49 (s, 3H, Ac); MS (CI+) m/e 193 (M+H+); Anal. calcd for C10H9FN2O: C, 62.49; H, 4.72; N, 14.58. Found: C, 62.50; H, 4.79; N, 14.63.

Workup

extractionextracted with CH2Cl2 (2×100 mL)
dry with materialThe extracts were dried (Na2SO4)
concentrationconcentrated
customthe residue recrystallised from hexane

Sources & evidence

ORD record: ord-ee0372cf6d574d90ba6a72497010b0bd
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665732

Reaction notes

Loading…