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Potassium Phosphate, Tribasic → (4-Benzyloxy-6-fluoro-1-methyl-naphthalen-2-yl)-acetic acid methyl ester

HRID 238622
Notes
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Reaction equation

HRID 238622 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[C:6]=1Br.[CH3:26]B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[C:6]=1[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 139377Methylboronic AcidHCID 59326473(4-Benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326512(4-Benzyloxy-6-fluoro-1-methyl-naphthalen-2-yl)-acetic acid methyl esterYield 59.5%

Reagents, catalysts & solvents

4
HCID 962WaterCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of (4-benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (100 mg, 0.248 mmol, prepared using an analogous procedure to the first step of example 5-1), methylboronic acid (19.3 mg, 0.322 mmol), potassium phosphate (184 mg, 0.868 mmol) and tricyclohexylphosphine (69.4 mg, 0.248 mmol) in toluene (4.0 mL) and water (2 drops) was added palladium acetate (3 mg, 0.0124 mmol) under a nitrogen atmosphere. After being heated under microwave conditions (150° C., 30 minutes), the mixture was cooled to room temperature, then diluted with water (10 mL), and extracted with ethyl acetate (15 mL×2). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (10% ethyl acetate in hexanes) to afford (4-benzyloxy-6-fluoro-1-methyl-naphthalen-2-yl)-acetic acid methyl ester (50 mg, 59.5%) as a light yellow solid.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (15 mL×2)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-102f8abdf2484b0f877039ad4dfadf42
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642629B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes