[C:1](Cl)([C:3](Cl)=O)=[O:2].CN(C=O)C.[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([C:22]#[N:23])[CH:21]=1)[NH:18][CH:17]=C2.CCOC(C)=O>C(Cl)Cl>[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([C:22]#[N:23])[CH:21]=1)[NH:18][CH:17]=[C:3]2[CH:1]=[O:2]To a solution of (COCl)2 (4 mL) in DCM (100 mL) at 0° C. was added a solution of DMF (4 mL) in DCM (50 mL) dropwise. Half an hour later, a solution of 5-fluoro-1H-indole-7-carbonitrile (D132) (7 g) in DCM (100 mL) was added. The reaction was allowed to warm to RT to form a yellow precipitate. After 5 hours the solvent was removed by evaporation, and then THF (100 mL) and 2 M aqueous NaOH (100 mL) solution were added to the residue obtained above. After being stirred for about 1 h, EtOAc (3×200 mL) was added, the organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to afford 5-fluoro-3-formyl-1H-indole-7-carbonitrile (D133) (8 g) as a yellow solid. δH (DMSO-d6, 400 MHz): 7.20 (1H, dd), 7.82 (1H, dd), 8.08 (1H, s), 9.64 (1H, s).
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