Bis(pinacolato)diborane → 1-Methyl-5-(5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-ylboronic acid

HRID 1918881Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:23]=[C:14]3[CH2:15][N:16]([CH:19]4[CH2:22][O:21][CH2:20]4)[CH2:17][CH2:18][N:13]3[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.CC1(C)C(C)(C)[O:28][B:27](B2OC(C)(C)C(C)(C)O2)[O:26]1.CC(O[K])=O>O1CCOCC1.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]>[CH3:8][N:6]1[C:5](=[O:9])[C:4]([NH:10][C:11]2[CH:23]=[C:14]3[CH2:15][N:16]([CH:19]4[CH2:22][O:21][CH2:20]4)[CH2:17][CH2:18][N:13]3[N:12]=2)=[CH:3][C:2]([B:27]([OH:28])[OH:26])=[CH:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-bromo-1-methyl-3-(5-(oxetan-3-yl)-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylamino)pyridin-2(1H)-one 252a (1 g, 2.64 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (2 g, 7.92 mmol) in dioxane (40 mL) was added PdCl2(dppf) (215 mg, 0.26 mmol) and CH3COOK (776 mg, 7.92 mmol). The mixture was stirred at 100° C. for 6 h under argon atmosphere. After reaction the mixture was filtered and evaporated in vacuo. The residue was purified by reverse phase combiflash eluting with 0.3% NH4HCO3 in 1:3 water/CH3CN to give 143a as a white solid (300 mg, 33%). MS: (M+H)+ 346.

Workup

customAfter reaction the mixture
filtrationwas filtered
customevaporated in vacuo
customThe residue was purified by reverse phase combiflash
washeluting with 0.3% NH4HCO3 in 1:3 water/CH3CN

Sources & evidence

ORD record: ord-27f5a590d1dc4ae097f13bc9debe8d17
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618107B2

Reaction notes

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