Diisopropylethylamine → (6-(3-Hydroxypyrrolidin-1-yl)pyridin-3-yl)boronic acid

HRID 57548

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:12]C(C)(C)C(C)(C)[O:9]2)=[CH:4][N:3]=1.[NH:17]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[OH:22][CH:19]1[CH2:20][CH2:21][N:17]([C:2]2[N:3]=[CH:4][C:5]([B:8]([OH:9])[OH:12])=[CH:6][CH:7]=2)[CH2:18]1

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (239 mg, 1 mmol) in NMP (2 mL) was added pyrrolidin-3-ol (174 mg, 2 mmol) and DIPEA (500 uL, 3 mmol), then the mixture was sealed in a microwave tube and heated in microwave reactor at 180° C. for 1.5 hours. TLC and LC-Ms showed the reaction had completed and the desired compound was detected. The reaction mixture was poured into 30 mL of H2O, and extracted with n-BuOH, washed with water and brine, concentrated and purified on TLC(CH2Cl2:MeOH=10:1) to give a white solid. MS (m/z): 209 (M+H)+

Workup

customthe mixture was sealed in a microwave tube

Sources & evidence

ORD record: ord-c94974a92f67473ebca3df8f66b61180
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434726B2

Linked notes

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