Sodium Carbonate → HCID 70244937, compound

HRID 380012Notes

Reaction equation

HRID 380012 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.Br[C:24]1[C:25]([O:32][CH3:33])=[CH:26][C:27]([Cl:31])=[C:28]([CH3:30])[CH:29]=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>[Cl:31][C:27]1[C:28]([CH3:30])=[CH:29][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)=[C:25]([O:32][CH3:33])[CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 222672371-Bromo-4-chloro-2-methoxy-5-methylbenzeneHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

Product 1

HCID 70244937HCID 70244937, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.15 g, Example 33), 5-bromo-2-chloro-4-methoxytoluene (0.12 g), 2M aqueous sodium carbonate (0.57 ml) and tetrakis(triphenylphosphine)palladium (0) (0.014 g) in ethanol (5 ml) with heating at 90° C. for 4 hours. After work up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-10% ethanol in dichloromethane to give the title compound as an oil (0.13 g).

Workup

  1. customPrepared
  2. customAfter work up, the residue was purified by normal-phase HPLC
  3. washeluting with a gradient of 0-10% ethanol in dichloromethane

Sources & evidence

ORD record
ord-8beecce32fd845fea4faa8ff58a2a94a
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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