4-Bromo-6-(trifluoromethyl)-1H-indazole → methyl 3-fluoro-4-(6-(trifluoromethyl)-1H-indazol-4-yl)benzoate

HRID 58064

Reaction equation

Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[F:15][C:16]1[CH:21]=[C:20]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:18][C:17]=1B(O)O>O1CCOCC1.C([O-])(O)=O.[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:15][C:16]1[CH:21]=[C:20]([CH:19]=[CH:18][C:17]=1[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2)[C:22]([O:24][CH3:25])=[O:23]

Participants

Conditions

Temperature: 140 °C

Procedure

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.402 g, 1.515 mmol), (2-fluoro-4-(methoxycarbonyl)phenyl)boronic acid (0.3 g, 1.515 mmol) and PdCl2(dppf) (0.055 g, 0.076 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light yellow suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated. The crude residue was diluted with EtOAc and washed with water, dried over Na2SO4, and the volatiles were removed via rotary evaporation to give the title compound, which was used without further purification (0.4 g, 78%). ESI-MS m/z [M+H]+ calc'd for C16H10F4N2O2, 339.1. found 339.1.

Workup

concentrationThe reaction mixture was subsequently concentrated
additionThe crude residue was diluted with EtOAc
washwashed with water
dry with materialdried over Na2SO4
customthe volatiles were removed via rotary evaporation

Sources & evidence

ORD record: ord-d3a1dd7dfe19445db35b6d513b26417e
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434743B2

Linked notes

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