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Cesium carbonate → 5-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-carboxylic acid

HRID 1364487
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1364487
I[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11].C(C1SC(C2SC(NC(=O)C)=NC=2C)=CC=1)=O.OB(O)[C:31]1[S:35][C:34]([C:36]([OH:38])=[O:37])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CN(C=O)C>[C:8]([NH:7][C:5]1[S:6][C:2]([C:31]2[S:35][C:34]([C:36]([OH:38])=[O:37])=[CH:33][CH:32]=2)=[C:3]([CH3:11])[N:4]=1)(=[O:10])[CH3:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 27798075-Boronothiophene-2-carboxylic acidHCID 11993393Acetamide, N-[5-(5-formyl-2-thienyl)-4-methyl-2-thiazolyl]-HCID 57417074N-(5-Iodo-4-methyl-2-thiazolyl)acetamide

Produkt 1

HCID 119933965-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide, Intermediate 1 (550 mg; 1.95 mmol; 1 eq.), 5-(dihydroxyboryl)-2-thiophenecarboxylic acid (335.3 mg; 1.95 mmol; 1 eq.), cesium carbonate (1397.5 mg; 4.29 mmol; 2.20 eq.), Pd(dppf)Cl2 (57.1 mg; 0.08 mmol; 0.04 eq.) are put in a microwave reactor, followed by DMF (8 ml) and water (4 ml). The reaction mixture is flushed with argon and is heated under microwave action for 10 min at 150° C. It is filtered through a paper filter, diluted with HCl 1N solution (10 ml) and the desired product is extracted with EtOAc. Combined organic layer is dried over MgSO4, filtered and evaporated. The crude product is purified by preparative HPLC, affording Compound (4) as white-off solid (125 mg; 22.7%). 1H NMR (DMSO-d6) δ 2.14 (s, 3H), 2.44 (s, 3H), 7.21 (d, J=3.8 Hz, 1H), 7.67 (d, J=3.8 Hz, 1H), 12.30 (s, 1H), 13.15 (br s, 1H). M−(ESI): 281; M+(ESI): 283. HPLC, Rt: 2.54 min (purity: 99.9%).

Aufarbeitung

  1. customThe reaction mixture is flushed with argon
  2. filtrationIt is filtered through a paper
  3. filtrationfilter
  4. additiondiluted with HCl 1N solution (10 ml)
  5. extractionthe desired product is extracted with EtOAc
  6. dry with materialCombined organic layer is dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-27b9f77766ed4159aa70e52e219e1c2f
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07888379B2

Notizen zur Reaktion

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