Potassium Carbonate → N,N-diethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanamine

HRID 1947975Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.Cl[CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:17]([N:18]([CH2:21][CH3:22])[CH2:19][CH2:20][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1)[CH3:16]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (500 mg, 2.5 mmol) in DMF (10 mL) was added (2-chloroethyl)diethylamine (Compound 175B, 0.6 g, 4 mmol) and K2CO3 (1.38 g, 10 mmol). The reaction mixture was stirred at 140° C. for 1.5 h in a microwave reactor, then concentrated, residue was purified by HPLC to afford 100 mg of the title compound (yield: 12%). 1H NMR (DMSO-d6, 400 MHz): δ=1.1-1.2 (m, 9H), 1.25 (s, 12H), 2.72 (s, 0.5H), 2.75 (s, 1H), 3.00-3.10 (s, 4H), 3.1-3.2 (m, 2H), 3.44 (s, 3H), 4.58-4.59 (br, 3H), 7.74 (s, 1H), 7.82 (s, 0.5H), 8.05 (s, 0.5H), 8.09 (s, 1H).

Workup

concentrationconcentrated
customresidue was purified by HPLC

Sources & evidence

ORD record: ord-ff9b846702d84cd8bcc503d48dd11f62
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399433B2

Reaction notes

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