Potassium Carbonate → HCID 178438833, compound

HRID 1947197Notes

Reaction equation

HRID 1947197 reaction equation
[CH:1]([C:4]1[C:5]([O:33]CC=C)=[CH:6][C:7]([O:29]CC=C)=[C:8]([C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:18][CH:17]=3)[C:12]([OH:15])=[N:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>[OH:15][C:12]1[N:11]([C:16]2[CH:17]=[CH:18][C:19]([CH2:22][N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:20][CH:21]=2)[C:10]([C:8]2[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]([OH:33])=[CH:6][C:7]=2[OH:29])=[N:14][N:13]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178458729HCID 178458729, compound

Product 1

HCID 178438833HCID 178438833, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolvent

Procedure

A methanol solution of 5-(5-isopropyl-2,4-bis-allyloxy-phenyl)-4-[4-(morpholin-4-ylmethyl)-phenyl]-4H-[1,2,4]triazol-3-ol (37.9 mg, 0.077 mmol) was mixed with tetrakis(triphenylphosphine) palladium (7 mg, 0.007 mmol) and potassium carbonate (64 mg, 0.46 mmol) and reacted at 80° C. for 12 hours. The residue obtained after the concentration was purified by silica gel column chromatography (dichloromethane:methanol 15:1-10:1) to obtain the title compound (OH-a02: white solid, 4.5 mg, 14%).

Workup

  1. customreacted at 80° C. for 12 hours
  2. customThe residue obtained
  3. concentrationafter the concentration
  4. customwas purified by silica gel column chromatography (dichloromethane:methanol 15:1-10:1)

Sources & evidence

ORD record
ord-0d162d90a20a4ee29de155c457ff21cf
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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