HCID 67810950, compound → (1-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]methyl}cyclopropyl)methanol

HRID 2279892Notes

Reaction equation

C([O:8][CH2:9][C:10]1([CH2:13][N:14]2[CH:18]=[C:17]([B:19]3[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]3)[CH:16]=[N:15]2)[CH2:12][CH2:11]1)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:26][C:21]1([CH3:27])[C:22]([CH3:24])([CH3:25])[O:23][B:19]([C:17]2[CH:16]=[N:15][N:14]([CH2:13][C:10]3([CH2:9][OH:8])[CH2:12][CH2:11]3)[CH:18]=2)[O:20]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of −({1-[(benzyloxy)methyl]cyclopropyl}methyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 63C, 8 g, 21.7 mmol) in ethanol (100 mL) was treated with palladium on charcoal (10%, 6 g) and heated to 50° C. under hydrogen atmosphere for 24 hrs. The catalyst was filtered off and the filtrate was concentrated to a residue under reduced pressure. The residue was triturated with isopropyl ether to give 3.2 g (53%) of the required material as white solid. 1H NMR (500 MHz, CDCl3) δ 7.81 (s, 1H), 7.7 (s, 1H), 4.14 (s, 2H), 3.38 (s, 2H), 1.33 (s, 12H), 0.54-0.65 (m, 4H).

Workup

filtrationThe catalyst was filtered off
concentrationthe filtrate was concentrated to a residue under reduced pressure
customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record: ord-64729e8adcb249178f984317b52424bc
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133224B2

Reaction notes

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