1-(3-(Benzyloxy)propyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol

HRID 2279713Notes

Reaction equation

HRID 2279713 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([B:17]2[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]2)[CH:14]=[N:13]1)C1C=CC=CC=1>CCO.[Pd]>[CH3:24][C:19]1([CH3:25])[C:20]([CH3:22])([CH3:23])[O:21][B:17]([C:15]2[CH:14]=[N:13][N:12]([CH2:11][CH2:10][CH2:9][OH:8])[CH:16]=2)[O:18]1

Participants

4

Reactant 1

HCID 866976811-(3-(Benzyloxy)propyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 671871273-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A deoxygenated mixture of 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 3F, 505 mg, 1.48 mmol) and 10% Pd—C (100 mg) in EtOH (15 mL) was stirred under an atmosphere of hydrogen overnight. The reaction mixture was filtered through a pad of celite and evaporated under reduced pressure to give the desired product as 370 mg of a light-yellow oil (99%). 1H NMR (CDCl3, 400 MHz): δ=7.80 (s, 1H), 7.71 (s, 1H), 4.32 (t, J=6.3 Hz, 2H), 3.63 (t, J=5.8 Hz, 2H), 2.06 (m, 3H), 1.33 (s, 12H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a53a1c61e07b43b6a0188fb05f1301ef
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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