Toluene → HCID 59326614, compound

HRID 238636Notes

Reaction equation

HRID 238636 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])=[CH:18][N:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10](Br)[CH:11]=2)[CH:6]=1.[CH3:29]B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>O.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>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])=[CH:18][N:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:29])[CH:11]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 59326566HCID 59326566, compound

Product 1

HCID 59326614HCID 59326614, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of [6-bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-acetic acid methyl ester (30 mg, 0.07 mmol, methyl ester of example 12-1), methylboronic acid (7 mg, 0.11 mmol), tetrakis(triphenylphosphine)palladium(0) (8 mg, 0.007 mmol), potassium phosphate (45 mg, 0.21 mmol) and toluene (0.5 mL) was stirred at 115 overnight under an argon atmosphere. The resulting mixture was diluted with water (5 mL), and then extracted with ethyl acetate (20 mL×2). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (20% ethyl acetate in petroleum ether) to give [4-(5-ethanesulfonyl-pyridin-2-yloxy)-6-methyl-naphthalen-2-yl]-acetic acid methyl ester (20 mg) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate (20 mL×2)
  2. washThe combined organic layers were washed with brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-6976400e15c446338f9a4ecba4620a0e
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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