Pyridine → Benzyl 3-bromo-6-{[(4-fluorophenyl)sulfonyl]amino}-2-methylbenzoate

HRID 1725927

Reaktionsgleichung

Reaktionsgleichung von HRID 1725927
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:6]([CH3:18])[C:5]([Br:19])=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.N1C=CC=CC=1>ClCCl>[Br:19][C:5]1[C:6]([CH3:18])=[C:7]([C:2]([NH:1][S:27]([C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)(=[O:29])=[O:28])=[CH:3][CH:4]=1)[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 68863679Benzyl 6-amino-3-bromo-2-methylbenzoate

Produkt 1

HCID 68864112Benzyl 3-bromo-6-{[(4-fluorophenyl)sulfonyl]amino}-2-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of Example 126B (760 mg, 2.1 mmol), 4-fluorobenzenesulfonyl chloride (600 mg, 3.1 mmol), dichloromethane (10 mL), and pyridine (0.69 mL, 8.5 mmol) was stirred for 18 hours, diluted with dichloromethane (100 mL), washed with 0.5M HCl (2×100 mL) and brine, dried (Na2SO4), filtered, concentrated and purified on a Biotage silica gel cartridge (40 g) eluted with 50-75% dichloromethane/hexanes to provide the desired product. MS (ESI(+) lm/e 478, 480 (M+H)+, 495, 497 (M+NH4)+, 500, 502 (M+Na)+; (ESI(−)) m/e 476, 478 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.09 (s, 1H), 7.73 (m, 2H), 7.62 (d, 1H), 7.40 (m, 7H), 6.85 (d, 1H), 5.25 (s, 2H), 2.19 (s, 3H).

Aufarbeitung

  1. washwashed with 0.5M HCl (2×100 mL) and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on a Biotage silica gel cartridge (40 g)
  6. washeluted with 50-75% dichloromethane/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-037a1b25943b442889049d6cc260e22c
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491718B2

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