Sodium Carbonate → HCID 53829171, compound

HRID 1856702Notes

Reaction equation

HRID 1856702 reaction equation
[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.I[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([O:30][CH3:31])[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C(O)C>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([C:8]2[CH:9]=[CH:10][C:5]([O:4][C@@H:3]([CH3:14])[C@H:2]([OH:1])[CH2:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:6][CH:7]=2)[CH:29]=[CH:28][N:27]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 150197954-Iodo-2-methoxypyridineHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

Product 1

HCID 53829171HCID 53829171, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Prepared according to the method described in Example 21b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.150 g, Example 21a), 4-iodo-2-methoxypyridine (0.235 g, Liebigs Annalen der Chemie (1992) Issue 9, 953-9), ethanol (3 ml), 2M aqueous sodium carbonate (0.5 ml) and tetrakis(triphenylphosphine)palladium(0) (0.025 g) with heating at 90° C. for 4 hours. After work up, the residue was purified by normal-phase HPLC, eluting with a gradient of 0-25% ethanol in dichloromethane to give the title compound as an oil (0.069 g).

Workup

  1. customPrepared
  2. customAfter work up, the residue was purified by normal-phase HPLC
  3. washeluting with a gradient of 0-25% ethanol in dichloromethane

Sources & evidence

ORD record
ord-cfe81aee9e234e3a826493e6bf47e74c
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

Loading…