Ethanol → HCID 69423098, compound

HRID 350235Notes

Reaction equation

HRID 350235 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[C:17]([CH2:19][N:20]4[CH:24]=[C:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:32][CH2:33][CH3:34])=[N:21]4)[CH:16]=[CH:15][N: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>[CH2:33]([O:32][C:22]1[C:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:24][N:20]([CH2:19][C:17]2[CH:16]=[CH:15][N:14]=[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:18]=2)[N:21]=1)[CH3:34]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86760430HCID 86760430, compound

Product 1

HCID 69423098HCID 69423098, compoundYield 99%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of ethyl 3-[1-[2-(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)-4-pyridylmethyl]-3-ethoxy-1H-pyrazol-4-yl]propionate (968 mg), phenylboronic acid (280 mg), tetrakis(triphenylphosphine)palladium (57.8 mg), sodium carbonate (488 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-[2-(5-phenylimidazo[1,2-a]pyridin-2-ylmethoxy)-4-pyridylmethyl]-1H-pyrazol-4-yl]propionate (1040 mg, yield: 99%) as a colorless oily substance from the fraction eluted with ethyl acetate.

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-871292e529a645af89f46c37cc22052f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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