[4-(Methoxycarbonyl)-2-methylphenyl]boronic acid → HCID 89782937, compound

HRID 58065

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.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[C:21]([CH3:28])[CH:20]=1)=[O:18]>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]>[CH3:28][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=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:17]([O:16][CH3:15])=[O:18]

Participants

Conditions

Temperature: 140 °C

Procedure

To a microwave vial was added a mixture 4-bromo-6-(trifluoromethyl)-1H-indazole (0.478 g, 1.804 mmol), (4-(methoxycarbonyl)-2-methylphenyl)boronic acid (0.35 g, 1.804 mmol) and PdCl2(dppf) (0.066 g, 0.090 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light yellow suspension was heated at 140° C. for 60 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the residue was diluted with EtOAc and washed with water. The volatiles were removed via rotary evaporation to give the title compound, which was used without further purification (0.53 g). ESI-MS m/z [M+H]+ calc'd for C17H13F3N2O2, 335.1. found 335.2.

Workup

concentrationThe reaction mixture was subsequently concentrated
additionthe residue was diluted with EtOAc
washwashed with water
customThe volatiles were removed via rotary evaporation

Sources & evidence

ORD record: ord-baa272f5ec214d7b956cc5f094773292
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434743B2

Linked notes

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