Ethanol → HCID 23024882, compound

HRID 350229Notes

Reaction equation

HRID 350229 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:34]=[CH:33][C:16]([CH2:17][N:18]4[CH:22]=[C:21]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:30][CH2:31][CH3:32])=[N:19]4)=[CH:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[CH2:31]([O:30][C:20]1[C:21]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:22][N:18]([CH2:17][C:16]2[CH:33]=[CH:34][C:13]([O:12][CH2:11][C:9]3[N:10]=[C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[N:7]4[CH:8]=3)=[CH:14][CH:15]=2)[N:19]=1)[CH3:32]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86760429HCID 86760429, compound

Product 1

HCID 23024882HCID 23024882, compoundYield 96.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 3-[1-[4-(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)benzyl]-3-ethoxy-1H-pyrazol-4-yl]propionate (676 mg), phenylboronic acid (195 mg), tetrakis(triphenylphosphine)palladium (40.4 mg), sodium carbonate (339 mg), ethanol (3 ml), water (3 ml) and toluene (15 ml) was refluxed overnight under an argon atmosphere. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 3-[3-ethoxy-1-[4-(5-phenylimidazo[1,2-a]pyridin-2-ylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (707 mg, yield: 96%) as colorless crystals from the fraction eluted with ethyl acetate. This was recrystallized from ethyl acetate-hexane. Melting point: 104–105° C.

Workup

  1. temperaturewas refluxed overnight under an argon atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d8c490477bd54c0fbe64f2caa445d5d8
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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