Tributylphosphine → HCID 23159849, compound

HRID 2110909Notes

Reaction equation

HRID 2110909 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:28][C:29]1[CH:34]=[C:33](O)[CH:32]=[CH:31][C:30]=1[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[C:1]([C:5]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][O:27][C:33]3[CH:32]=[CH:31][C:30]([CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:29]([F:28])[CH:34]=3)=[CH:22][CH:21]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23082888Ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoateHCID 23157612HCID 23157612, compound

Product 1

HCID 23159849HCID 23159849, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of [4-({3-tert-butyl-5-[(6-methylpyridin-2-yl)methoxy]-1H-pyrazol-1-yl}methyl)phenyl]methanol (0.80 g, 2.2 mmol), ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoate (0.49 g, 2.3 mmol), tributylphosphine (1.10 mL, 4.41 mmol) and tetrahydrofuran (40 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.11 g, 4.40 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated under reduced pressure, 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 (1.11 g, yield 90%) as a yellow oil. MS: m/z 560 (MH+).

Workup

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

Sources & evidence

ORD record
ord-3b1e6d9e2028403c9d9d93121de80519
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

Loading…