Sodium Carbonate → 1-(4-chloro-2-trifluoromethylbenzyl)-3-(4-fluorophenyl)-1H-indazole-5-carbaldehyde

HRID 2401008Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=2)[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[C:21]([F:24])([F:23])[F:22])[N:3]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:4]2[C:5]3[C:10](=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=3)[C:2]([C:29]3[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=3)=[N:3]2)=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-bromo-1-(4-chloro-2-trifluoromethylbenzyl)-1H-indazole-5-carbaldehyde (0.311 mmol from Example 407), 4-fluorophenylboronic acid (0.498 mmol), Pd(dppf)Cl2 dichloromethane complex (0.0311 mmol) and sodium carbonate (0.933 mmol) in DME/H2O (4 mL; 4:1) under argon was stirred at 100° C. for 6 h, then concentrated. The residue was purified by chromatography (silica gel, hexanes to hexanes:EtOAc, 1:1) to afford 1-(4-chloro-2-trifluoromethylbenzyl)-3-(4-fluorophenyl)-1H-indazole-5-carbaldehyde as white solid.

Workup

concentrationconcentrated
customThe residue was purified by chromatography (silica gel, hexanes to hexanes:EtOAc, 1:1)

Sources & evidence

ORD record: ord-9002798d8d5b4c5d922f77f5c7c7748a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796256B2

Reaction notes

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