Barium hydroxide → Tert-butyl{3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(3-methoxypropyl)-3,6'-dimethylbiphenyl-4-yl]propyl}carbamate

HRID 2194901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194901
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][C:29]3[C:34]([Cl:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=3[Cl:37])=[CH:21][CH:20]=2)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:4]([CH3:38])[CH:3]=1.[CH3:39][O:40][CH2:41][CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH3:50])[C:45]=1B(O)O.C(COC)OC.O.[OH-].[Ba+2].[OH-]>O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:13]([O:12][C:11](=[O:17])[NH:10][CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([C:45]2[C:46]([CH3:50])=[CH:47][CH:48]=[CH:49][C:44]=2[CH2:43][CH2:42][CH2:41][O:40][CH3:39])=[CH:3][C:4]=1[CH3:38])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][C:29]2[C:30]([Cl:37])=[CH:31][C:32]([CH3:36])=[CH:33][C:34]=2[Cl:35])=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14]

Komponenten

7

Edukt 4

HCID 6093286Barium hydroxideHCID 18180031Water 1,2-dimethoxyethaneHCID 58083342[2-(3-Methoxypropyl)-6-methylphenyl]boronic acidHCID 86658849Tert-butyl (2-(4-bromo-2-methylphenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propyl)carbamate

Produkt 1

HCID 131730111Tert-butyl{3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(3-methoxypropyl)-3,6'-dimethylbiphenyl-4-yl]propyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution tert-butyl (2-(4-bromo-2-methylphenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propyl)carbamate from EXAMPLE 2, step 2 (1 eq.) and [2-(3-methoxypropyl)-6-methylphenyl]boronic acid from step 1 (1.1 eq.) in 1-2 dimethoxyethane/water (6/1; 0.1M) at room temperature was added palladium tetrakis(triphenylphosphine) (0.05 eq.) and Barium hydroxide (1.5 eq.). The mixture was stiffed at 80° C. for 5 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (10 to 70%, in 30 min) afforded the desired compound.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  8. washeluting with Hex/EtOAc (10 to 70%, in 30 min)

Quellen und Nachweise

ORD-Eintrag
ord-4d23e93d73854215a67c44ef0142da61
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334308B2

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