4-bromo-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide → 1-(4-(N-thiazol-2-ylsulfamoyl)-phenyl)pyrrolidine-3-carboxylic acid

HRID 2043172

Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:17]1[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18]1.O(C(C)(C)C)[Na].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[S:13]1[CH:14]=[CH:15][N:16]=[C:12]1[NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([N:17]2[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18]2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Prepared using general procedure 31. A mixture of 4-bromo-N-(thiazol-2-yl)benzenesulfonamide (4.70 g, 14.7 mmol), pyrrolidine-3-carboxylic acid (3.66 g, 22.1 mmol, 1.5 eq.), NaO-t-Bu (7.62 g, 79.3 mmol, 5.4 eq.), 2-(dicyclohexylphosphino)-2′,6′-dimethoxybiphenyl (0.722 g, 1.76 mmol, 12 mol %) and tris(dibenzylideneacetone)-dipalladium (0.40 g, 3 mol %) in toluene (45 mL) was heated at 100° C. for 20 hours. The brown suspension was cooled to room temperature. Purification via silica gel chromatography using 1-10% MeOH in CH2Cl2 gave 1-(4-(N-thiazol-2-ylsulfamoyl)-phenyl)pyrrolidine-3-carboxylic acid (2.26 g, 43%). 1H NMR (300 MHz, DMSO-d6): δ 7.55 (d, J=8 Hz, 2H); 7.17 (dd, J=4.7, 1.1 Hz, 1H); 6.73 (dd, J=4.7, 1.1 Hz, 1H); 6.55 (d, J=8 Hz, 2H); 3.50-3.23 (m, 4H, partly obscured by water from DMSO-d6); 3.20-3.15 (m, 1H); 2.23-2.09 (m, 2H).

Aufarbeitung

customPrepared
temperatureThe brown suspension was cooled to room temperature
customPurification via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-bcc0ebaf570e4488921499673aa4fafb
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08586589B2

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