Methanesulfonyl chloride → 1-(methylsulfonyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine

HRID 389457Notes

Reaction equation

Cl.[CH3:2][C:3]1([CH3:21])[C:7]([CH3:9])([CH3:8])[O:6][B:5]([C:10]2[CH:11]=[N:12][N:13]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:14]=2)[O:4]1.CCN(C(C)C)C(C)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH3:31][S:32]([N:18]1[CH2:19][CH2:20][CH:15]([N:13]2[CH:14]=[C:10]([B:5]3[O:6][C:7]([CH3:8])([CH3:9])[C:3]([CH3:21])([CH3:2])[O:4]3)[CH:11]=[N:12]2)[CH2:16][CH2:17]1)(=[O:34])=[O:33]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine hydrochloride (200 mg, 0.64 mmol) in DCM (4 mL) was cooled to 0° C. and treated with DIPEA (280 μL, 1.6 mmol). Methanesulfonyl chloride (74 μL, 0.96 mmol) was added dropwise slowly and the mixture was stirred at RT for 18 hours. The mixture was concentrated in vacuo, taken up in MeOH and purified by MDP to afford 100 mg (40%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 1.34 (s, 12H) 2.05-2.22 (m, 2H) 2.22-2.34 (m, 2H) 2.81-2.90 (m, 4H) 2.90-3.04 (m, 3H) 3.86-4.03 (m, 2H) 4.26-4.43 (m, 1H) 7.77 (s, 1H) 7.81-7.90 (m, 1H).

Workup

concentrationThe mixture was concentrated in vacuo
custompurified by MDP

Sources & evidence

ORD record: ord-e83d7ab9ed3a45ca97fe255837ae69c7
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

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