(4-Fluoro-3-methylphenyl)boronic acid → 2-(3-(4-Fluoro-3-methyl-phenyl)-5-phenyl-(1,2,4)triazol-1-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone

HRID 336388

Reaction equation

Br[C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([CH2:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[N:3]=1.C(OC([O-])=O)([O-])=O.[Na+].[Na+].[F:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][C:39]=1[CH3:47]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:37][C:38]1[CH:43]=[CH:42][C:41]([C:2]2[N:6]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH2:13][C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[N:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:18][CH2:17]3)=[O:15])[N:3]=2)=[CH:40][C:39]=1[CH3:47]

Participants

Conditions

Temperature: 120 °C

Procedure

15 mg tetrakis(triphenylphosphine)palladium(0) was added to 100 mg 2-(3-bromo-5-phenyl-(1,2,4)triazol-1-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone, 500 μL 2 mol/L aqueous sodiumdicarbonate solution and 43 mg 4-fluoro-3-methylphenylboronic acid in 10 mL dioxane under nitrogen. The reaction was stirred over night at 120° C. The reaction was filltered and evaporated. The residue was purified by HPLC to give 32 mg of the desired product.

Workup

customevaporated
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-84aea2a5210d410c990142fca04841a1
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889677B2

Linked notes

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