4-(tert-Butoxycarbonylaminomethyl)phenylboronic acid, pinacol ester → HCID 66823422, compound

HRID 2362155Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:14]=[CH:15][N:16]=[C:4]2[N:3]=1.[C:17]([O:21][C:22](=[O:40])[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][CH:26]=1)([CH3:20])([CH3:19])[CH3:18]>O1CCOCC1.C(Cl)Cl.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[C:17]([O:21][C:22](=[O:40])[NH:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:2]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][N:5]3[N:14]=[CH:15][N:16]=[C:4]3[N:3]=2)=[CH:29][CH:30]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of compound 3-4 (60 mg 0.24 mmol), [4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-carbamic acid tert-butyl ester (100 mg, 0.3 mmol), aq.Na2 CO3 (2M, 0.70 mmol, 0.35 mL) and Pd(DPPF)Cl2 (10 mg) in dioxane (3 mL) was heated at 100° C. in microwave system under N2 atmosphere for 30 min. After cooling, the mixture was diluted with 15 mL of DCM, the combined organic phase was washed with 0.1N HClaq and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 46 mg of 3-5. MS (ESI) m/e (M+H) 402.1

Workup

temperatureAfter cooling
washthe combined organic phase was washed with 0.1N HClaq and brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customThe residue was purified by prep.TLC

Sources & evidence

ORD record: ord-231124078f7145929bf5e49b067c721f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691825B2

Reaction notes

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