Sodium Carbonate → (3R,4S)-4-[4-(2-Methoxypyridin-3-yl)phenoxy]-1-pyridin-3-yl-pentan-3-ol

HRID 1856700Notes

Reaction equation

HRID 1856700 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[OH:7][C@H:8]([CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[C@H:9]([CH3:20])[O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.I[C:30]1[C:31]([O:36][CH3:37])=[N:32][CH:33]=[CH:34][CH:35]=1>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>[CH3:37][O:36][C:31]1[C:30]([C:14]2[CH:15]=[CH:16][C:11]([O:10][C@@H:9]([CH3:20])[C@H:8]([OH:7])[CH2:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:12][CH:13]=2)=[CH:35][CH:34]=[CH:33][N:32]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 70094973-Iodo-2-methoxypyridineHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

Product 1

HCID 53881374(3R,4S)-4-[4-(2-Methoxypyridin-3-yl)phenoxy]-1-pyridin-3-yl-pentan-3-ol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Prepared according to the method described in Example 21b) from 2M aqueous sodium carbonate (2.0 ml), (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (Example 21a), 0.508 g), 3-iodo-2-methoxypyridine (0.730 g, J. Org. Chem., 1988 53(12), 2740), and tetrakis(triphenylphosphine)palladium(0) (0.216 g) in ethanol (10 ml). The mixture was heated at reflux for 6 hours. After cooling to room temperature the mixture was concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate to give an oil, which was further purified by normal phase HPLC eluting with 2-propanol:dichloromethane (3:97) to give the title compound as an oil.

Workup

  1. customPrepared
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 6 hours
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica eluting with ethyl acetate
  6. customto give an oil, which
  7. customwas further purified by normal phase HPLC
  8. washeluting with 2-propanol:dichloromethane (3:97)

Sources & evidence

ORD record
ord-13ac3cea18514ce4bbe87e682f2d81c3
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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