Acetyl chloride → 1-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidin-1-yl)ethanone

HRID 389458Notes

Reaction equation

HRID 389458 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.[C:22](Cl)(=[O:24])[CH3:23].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:2][C:3]1([CH3:21])[C:7]([CH3:8])([CH3:9])[O:6][B:5]([C:10]2[CH:11]=[N:12][N:13]([CH:15]3[CH2:20][CH2:19][N:18]([C:22](=[O:24])[CH3:23])[CH2:17][CH2:16]3)[CH:14]=2)[O:4]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 667591824-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine hydrochloride

Product 1

HCID 593927031-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidin-1-yl)ethanoneYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine hydrochloride (3.66 g, 11.7 mmol) in DMF (109.8 mL) was charged with acetyl chloride (0.91 mL, 12.84 mmol) and DIPEA (5.08 mL, 29.17 mmol) at 0° C. and left to warm up to RT in an ice bath overnight. The crude product was concentrated in vacuo to a solid and purified by flash chromatography (0 to 5% MeOH:EtOAc) to afford 3.71 g (99%) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 7.97 (s, 1H), 7.59 (s, 1H), 4.38-4.48 (m, 2H), 3.85-3.94 (m, 1H), 3.13-3.22 (m, 1H), 2.69 (td, J=12.8, 2.7 Hz, 1H), 2.03 (s, 3H), 1.81-2.02 (m, 3H), 1.72 (qd, J=12.1, 4.6 Hz, 1H), 1.24 (s, 12H).

Workup

  1. waitleft
  2. concentrationThe crude product was concentrated in vacuo to a solid
  3. custompurified by flash chromatography (0 to 5% MeOH:EtOAc)

Sources & evidence

ORD record
ord-ecf8192ed7ea4e8890a32fbca7dd60c2
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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