Potassium Phosphate, Tribasic → {4-[7-(4-Methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-thiazol-2-ylmethyl}-carbamic acid tert-butyl ester

HRID 1446677

Reaktionsgleichung

Reaktionsgleichung von HRID 1446677
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[N:18]3[CH:19]=[CH:20][C:21](Cl)=[CH:22][C:17]3=[N:16][CH:15]=2)[N:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][S:26]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)(=[O:28])=[O:27].[O-]P([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCOCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[N:18]3[CH:19]=[CH:20][C:21]([C:32]4[CH:33]=[CH:34][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:30][CH:31]=4)=[CH:22][C:17]3=[N:16][CH:15]=2)[N:13]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 68545966[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-thiazol-2-ylmethyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 68544439{4-[7-(4-Methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-thiazol-2-ylmethyl}-carbamic acid tert-butyl esterAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of [4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-thiazol-2-ylmethyl]-carbamic acid tert-butyl ester (0.180 g, 0.49 mmol, 1.0 eq.) in dioxane/water (2:1, 6 mL), add 4-(methylsulphonyl)-benzeneboronic acid (0.108 g, 1.1 eq.), K3PO4 (0.208 g, 2.0 eq.), S-phos (0.025 g, 12.5% eq.) and Pd(OAc)2 (0.006 g, 0.05 eq.). Deoxygenate the reaction mixture and fill with nitrogen and stir at 100° C. for 4 hours. Cool the mixture to room temperature and dilute with 5:95 MeOH/DCM (100 mL). Wash the mixture with saturated aqueous saturated sodium chloride (2×20 mL), water (2×20 mL), dry, filter, and concentrate. Purify the residue on silica gel with a 0-80% EtOAc/Hexane gradient, then with 5:95 MeOH/DCM to give 0.160 g of the title compound as a slightly yellow solid.

Aufarbeitung

  1. customDeoxygenate the reaction mixture and fill with nitrogen
  2. temperatureCool the mixture to room temperature
  3. additiondilute with 5:95 MeOH/DCM (100 mL)
  4. washWash the mixture with saturated aqueous saturated sodium chloride (2×20 mL), water (2×20 mL)
  5. customdry
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the residue on silica gel with a 0-80% EtOAc/Hexane gradient

Quellen und Nachweise

ORD-Eintrag
ord-099ba786b7e440788150ab0207ede667
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666879B2

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