N-(6-Bromo-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamide → tert-butyl 4-[N-(5-acetamido-6-bromoindan-1-yl)amino]-2-fluorobenzoate

HRID 1297521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1297521
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[C:10](=O)[CH2:9][CH2:8]2)(=[O:3])[CH3:2].[NH2:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:19]([F:30])[CH:18]=1.[B][B][B][B][B][B][B][B][B][B]>CO>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[CH:10]([NH:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[C:19]([F:30])[CH:18]=1)[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 9993147N-(6-Bromo-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamideHCID 10058989Tert-butyl 4-amino-2-fluorobenzoateHCID 178419135HCID 178419135, Verbindung2×

Produkt 1

HCID 58915010tert-butyl 4-[N-(5-acetamido-6-bromoindan-1-yl)amino]-2-fluorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-acetamido-6-bromoindan-1-one (0.370 g, 1.38 mmol) in anhydrous methanol (32 ml) was added tert-butyl 4-amino-2-fluorobenzoate (V. Bavetsias et al, J. Med. Chem. 1996, 39, 73-85; 0.322 g, 1.52 mmol) followed by decaborane (0.030 g). The reaction mixture was stirred at room temperature for 11 hours then more decaborane (0.005 g) was added and stirring was continued for a longer 12 hours under argon. The solvent was removed in vacuo, and the residue was purified by column chromatography eluting with a gradient of ethyl acetate in hexane (30 to 40%). The desired compound was obtained as a white solid: 0.455 g (71%) m.p.>70° C. (softens); 1H-NMR (250 MHz, CDCl3, TMS) 1.57 (s, 9H, C(CH3)3), 2.24 (s, 3H, COCH3), 1.98, 2.56 (2×m, 2H, indanyl 2-H), 2.94 (m, 2H, indanyl 3-H), 4.33(d, J=7.90 Hz, 1H, N—H), 4.99 (q, J=7.06 Hz, 1H, indanyl 1-H), 6.37 (m, 2H, 3,5-H), 7.48, 8.25, 7.60 (3×s, each 1H, indanyl 4-H, 7-H, CONH), 7.72 (t, J=8.75 Hz, 6-H); MS (ESI, mz) 485, 487 {(M+Na)+, bromine isotopic pattern}.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for a longer 12 hours under argon
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography
  5. washeluting with a gradient of ethyl acetate in hexane (30 to 40%)

Quellen und Nachweise

ORD-Eintrag
ord-ea51119aa3794b29b5a68da7cfa79c50
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250511B2

Notizen zur Reaktion

Wird geladen…