Sodium Carbonate → ({2-Methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}butyl)oxy]phenyl}oxy)acetic acid

HRID 1391814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391814
Br[C:2]1[N:7]=[C:6]([CH:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([O:23]CC)=[O:22])=[C:15]([CH3:26])[CH:14]=2)[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][CH:3]=1.C1([C:33]2[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[CH:35][C:34]=2B(O)O)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:26][C:15]1[CH:14]=[C:13]([O:12][CH:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:34]3[CH:33]=[CH:38][C:37]([C:39]([F:42])([F:41])[F:40])=[CH:36][CH:35]=3)[N:7]=2)[CH2:9][CH2:10][CH3:11])[CH:18]=[CH:17][C:16]=1[O:19][CH2:20][C:21]([OH:23])=[O:22]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 58629817Ethyl [(4-{[1-(6-bromo-2-pyridinyl)butyl]oxy}-2-methylphenyl)oxy]acetateHCID 69207925[2-Phenyl-4-(trifluoromethyl)phenyl]boronic acid

Produkt 1

HCID 10366937({2-Methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}butyl)oxy]phenyl}oxy)acetic acidAusbeute 21,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A stirred solution of ethyl [(4-{[1-(6-bromo-2-pyridinyl)butyl]oxy}-2-methylphenyl)oxy]acetate (50 mg, 0.12 mmol) in DME (0.5 mL) was treated with phenyl 4-(triflouromethyl)benzeneboronic acid (23 mg, 0.12 mmol) followed by Pd(PPh3)4 (14 mg, 0.01 mmol) and a solution of Na2CO3 (38 mg, 0.36 mmol) in water (0.5 mL), and the resulting mixture was heated at 70° C. for 18 hours under nitrogen. The solvent was then removed under vacuum and the resulting mixture acidified with aqueous HCl (2M) and then partitioned between water and EtOAc, the layers separated and the organic layer reduced to an oil. Purification by mass directed auto-prep HPLC afforded the title compound (12 mg).

Aufarbeitung

  1. customThe solvent was then removed under vacuum
  2. custompartitioned between water and EtOAc
  3. customthe layers separated
  4. customPurification by mass

Quellen und Nachweise

ORD-Eintrag
ord-e79e50afda424ada8a54314d39c422ce
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338960B2

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