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Yield:1126425-15-7 86%

Reaction Conditions:

Stage #1: 5-bromo-6-fluoro-1H-indazolewith sodium hydride in tetrahydrofuran;mineral oil at 0; for 0.333333 h;
Stage #2: with n-butyllithium in tetrahydrofuran;hexane;mineral oil at -78; for 0.5 h;

Steps:

17 5.1.17 6-Fluoro-1H-indazole-5-carbaldehyde (20)

A solution of 19 (3.5 g, 16.28 mmol) in THF (200 mL) was treated with NaH (60% mineral oil, 1.17 g) at 0 °C and stirred at rt for 20 min. The reaction mixture was cooled to -78 °C and treated with BuLi (2.5 M in Hexanes, 8.14 mL) dropwise. The mixture was stirred at temperature for 30 min treated with DMF (64 mmols) and slowly warmed to rt when the viscous solution turn homogenous and stirring was efficient. Analysis of TLC (40% EtOAc/Hexanes) indicated complete conversion of starting material to product.
The reaction mixture was acidified with aqueous 1 M HCl and taken up in EtOAc (500 mL) washed with aqueous HCl (1 M, 100 mL), brine (100 mL) dried (MgSO₄), filtered concentrated in vacuo to yield 20 (2.3 g, 86%) ¹H NMR (400 MHz, D₆-DMSO) δ 13.52 (s, 1H), 10.16 (s, 1H), 8.37 (d, 1H, J = 6.7), 8.32 (s, 1H), 7.46 (d, 1H, J = 11.6 Hz).

References:

Venkatraman, Srikanth;Velazquez, Francisco;Gavalas, Stephen;Wu, Wanli;Chen, Kevin X.;Nair, Anilkumar G.;Bennett, Frank;Huang, Yuhua;Pinto, Patrick;Jiang, Yueheng;Selyutin, Oleg;Vibulbhan, Bancha;Zeng, Qingbei;Lesburg, Charles;Duca, Jose;Heimark, Larry;Huang, Hsueh-Cheng;Agrawal, Sony;Jiang, Chuan-Kui;Ferrari, Eric;Li, Cheng;Kozlowski, Joseph;Rosenblum, Stuart;Shih, Neng-Yang;George Njoroge [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 1,p. 447 - 458]

633327-11-4 Synthesis