Tributylphosphine → HCID 23159944, compound

HRID 2110871Notes

Reaction equation

HRID 2110871 reaction equation
[C:1]([C:5]1[CH2:9][C:8](=[O:10])[N:7]([CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23]1[N:28]=[C:27]([CH2:29]O)[CH:26]=[CH:25][CH:24]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[C:1]([C:5]1[CH:9]=[C:8]([O:10][CH2:29][C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:22])[N:28]=2)[N:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 707366-Methyl-2-pyridylmethanolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23160005HCID 23160005, compound

Product 1

HCID 23159944HCID 23159944, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-[(3-tert-butyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)methyl]benzoate (1.68 g, 5.83 mmol), (6-methylpyridin-2-yl)methanol (0.79 g, 6.4 mmol), tributylphosphine (2.90 mL, 11.6 mmol) and tetrahydrofuran (80 mL) was added 1,1′-(azodicarbonyl)dipiperidine (2.94 g, 11.7 mol), and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and diisopropyl ether was added to the residue. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=2:3) to give the title compound (2.14 g, yield 93%) as a yellow oil. 1H NMR (CDCl3) δ: 1.27 (9H, s), 2.54 (3H, s), 3.90 (3H, s), 5.11 (2H, s), 5.25 (2H, s), 5.47 (1H, s), 6.96 (1H, d, J=7.8 Hz), 7.06 (1H, d, J=7.8 Hz), 7.19 (2H, d, J=8.6 Hz), 7.51 (1H, t, J=7.7 Hz), 7.93-8.00 (2H, m).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiisopropyl ether was added to the residue
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-13fd1a49d6004d95a64c9e2c6c4a812a
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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