HCID 58824205, compound → HCID 18444556, compound

HRID 2266807Notes

Reaction equation

HRID 2266807 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([CH3:26])=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=3)=[CH:14][CH:13]=2)[CH:9]=1)=[O:4]>O1CCCC1>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[O:6][C:7]=3[CH3:26])=[CH:13][CH:14]=2)=[N:19][CH:20]=1

Participants

3

Reactant 1

HCID 58824205HCID 58824205, compound

Product 1

HCID 18444556HCID 18444556, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[4-(5-methoxy-pyridin-2-yl)-phenoxymethyl]-5-methyl-furan-2-carboxylic acid methyl ester (52) (118 mg, 0.33 mmoles) in dry tetrahydrofuran (10 ml) was treated with potassium trimethylsilanoate (260 mg, 2.0 mmoles) and the mixture stirred under an argon atmosphere for 2 hours. After evaporation of the solvent the residue was purified by HPLC (gradient: 18% acetonitrile/82% water containing 0.1% trifluoroacetic acid to 98% acetonitrile/2% water at a rate of 1%/min) to afford compound 53 (60 mg) as a white solid.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas purified by HPLC (gradient

Sources & evidence

ORD record
ord-32e7844f1a384dc8be047b6244cc187a
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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