Sodium Carbonate → HCID 53784232, compound

HRID 380013Notes

Reaction equation

HRID 380013 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[CH:29]=[CH:28][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[CH:26][CH:25]=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>[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]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[CH:26][CH:25]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 74654Benzeneacetic acid, 4-bromo-HCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

Product 1

HCID 53784232HCID 53784232, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °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 (0.6 g, Example 33), 4-bromophenylacetic acid (0.624 g), 2M aqueous sodium carbonate (2.5 ml) and tetrakis(triphenylphosphine)palladium (0) (0.5 g) in ethanol (15 ml). The reaction mixture was heated at 100° C. for 3 hours. After cooling, the solution was concentrated under reduced pressure. Water was added to the residue then washed with diethyl ether. The aqueous layer was acidified with 2M hydrochloric acid and washed with diethyl ether. The aqueous layer was neutralised to pH 7.11 and the solid filtered off washing with diethyl ether to give the title compound as a solid (0.431 g).

Workup

  1. customPrepared
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. washthen washed with diethyl ether
  6. washwashed with diethyl ether
  7. filtrationthe solid filtered off
  8. washwashing with diethyl ether

Sources & evidence

ORD record
ord-734119570f0a4495bc1271c6f8e375eb
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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