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

HRID 1956370Notes

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 CH2 Cl2 (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) δ8.05 (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 C10 H9FN2O: C, 62.49; H, 4.72; N, 14.58. Found: C, 62.50; H, 4.79; N, 14.63.

Workup

extractionextracted with CH2 Cl2 (2×100 mL)
dry with materialThe extracts were dried (Na2SO4)
concentrationconcentrated
customthe residue recrystallised from hexane

Sources & evidence

ORD record: ord-52c9dbfe1fe34f4986b575aa14416777
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780475

Reaction notes

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