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Triphenylphosphine → [4-(5-Ethanesulfonyl-3-ethyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 238650
Notes
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Reaction equation

HRID 238650 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([O:16][C:17]2[C:22](Br)=[CH:21][C:20]([S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[CH:19][N:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=2)[CH:6]=1.[CH2:31](B(O)O)[CH3:32].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([O:16][C:17]2[C:22]([CH2:31][CH3:32])=[CH:21][C:20]([S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[CH:19][N:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=2)[CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 521157Ethylboronic acidHCID 59326492[4-(3-Bromo-5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Product 1

HCID 59326586[4-(5-Ethanesulfonyl-3-ethyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester
Yield 47.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of [4-(3-bromo-5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (42 mg, 0.085 mmol), ethylboronic acid (15 mg, 0.20 mmol), bis(triphenylphosphine)dichloropalladium(II) (7.0 mg, 0.01 mmol), potassium phosphate (64 mg, 0.30 mmol), triphenylphosphine (15.2 mg, 0.05 mmol) and toluene (1 mL) was stirred at 100° C. overnight under an argon atmosphere. The resulting mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by preparative TLC (20% ethyl acetate in petroleum ether) to afford [4-(5-ethanesulfonyl-3-ethyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (18 mg, 47.6%) as a white solid.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by preparative TLC (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-cbf8dc933ca44dbaa04705673f6fb29c
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