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Potassium Phosphate, Tribasic → {6-Fluoro-3-methyl-4-[4-(toluene-2-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

HRID 1468354
Notes
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Reaction equation

HRID 1468354 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([S:15]([C:18]3[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)O1.[CH3:26][O:27][C:28](=[O:50])[CH2:29][C:30]1[C:39]([CH3:40])=[C:38](OS(C(F)(F)F)(=O)=O)[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([F:49])[CH:36]=2)[CH:31]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[Cl-].[Na+].O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH3:26][O:27][C:28](=[O:50])[CH2:29][C:30]1[C:39]([CH3:40])=[C:38]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([C:18]3[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:16])=[O:17])=[CH:13][CH:14]=2)[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([F:49])[CH:36]=2)[CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 59326772(6-Fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl esterHCID 866949484,4,5,5-Tetramethyl-2-[4-(toluene-2-sulfonyl)-phenyl]-[1,3,2]dioxaborolane

Product 1

HCID 86694947
{6-Fluoro-3-methyl-4-[4-(toluene-2-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester
Yield 31%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
125 °C

Procedure

To a mixture of 4,4,5,5-tetramethyl-2-[4-(toluene-2-sulfonyl)-phenyl]-[1,3,2]dioxaborolane (50 mg, 0.14 mmol), (6-fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (73 mg, 0.19 mmol), K3PO4 (81 mg, 0.38 mmol), palladium(II) acetate (14 mg, 0.06 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (49 mg, 0.12 mmol) were added anhydrous toluene (4 mL) and water (400 uL) at room temperature. The resulting light brown solution was heated to 125° C. for 15 hours. The reaction mixture was cooled to room temperature and diluted with brine solution and ethyl acetate. The two layers were separated and the aqueous layer was extracted with ethyl acetate and the combined extracts were washed with brine solution. The organic layer was dried over anhydrous MgSO4. Filtration and concentration gave a crude residue which was purified using an ISCO (40 g) column, eluting with 0-40% ethyl acetate in hexanes, to give {6-fluoro-3-methyl-4-[4-(toluene-2-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (20 mg, 31%). 1H NMR (300 MHz, CDCl3) δ ppm 8.31 (d, J=7.5 Hz, 1 H), 8.01 (d, J=7.8 Hz, 2 H), 7.80 (dd, J=8.5, 6.0 Hz, 1 H), 7.75 (s, 1 H), 7.50-7.62 (m, 1 H), 7.47 (d, J=7.5 Hz, 1 H), 7.40 (d, J=7.8 Hz, 2 H), 7.32 (d, J=7.2 Hz, 1 H), 7.19 (td, J=8.5, 2.0 Hz, 1 H), 6.72 (d, J=10.9 Hz, 1 H), 3.85 (s, 2 H), 3.73 (s, 3 H), 2.56 (s, 3 H), 2.09 (s, 3 H). HRMS calcd. for C27H24FO4S [(M+H)+] 463.1374, obsd. 463.1373.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe combined extracts were washed with brine solution
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationFiltration and concentration
  7. customgave a crude residue which
  8. customwas purified
  9. washeluting with 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-15ac5a4a82834d8bbdd1dd42f5726466
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09000044B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes