4-Acetylbenzoic Acid → tert-butyl 5-(4-acetylbenzamido)-1H-indole-2-carboxylate

HRID 1255962

Reaktionsgleichung

Reaktionsgleichung von HRID 1255962
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5]2.[C:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)(=[O:20])[CH3:19].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:5]3)=[O:26])=[CH:23][CH:22]=1)(=[O:20])[CH3:19]

Komponenten

6

Edukt 4

HCID 114704-Acetylbenzoic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 10633339Tert-butyl 5-amino-1H-indole-2-carboxylate

Produkt 1

HCID 59365009tert-butyl 5-(4-acetylbenzamido)-1H-indole-2-carboxylateAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 5-amino-1H-indole-2-carboxylate (220 mg, 0.94 mmol), 4-acetylbenzoic acid (155 mg, 0.94 mmol) and TBTU (303 mg, 0.94 mmol) in DMF (6 mL) at 4° C. was treated with diisopropylethylamine (329 uL, 1.89 mmol) and stirred 40 min at 0˜5° C. The solvent was removed under vacuo. The crude product was chromatographed on silica gel eluted with 1% MeOH in CH2Cl2 to give 2 (350 mg, 98%). 1HNMR DMSO-d6) δ11.66 (bs, 1H), 10.34 (s, 1H), 8.09 (d, 1H, J=8.8 Hz), 8.07 (s, 4H), 7.55 (d, 1H, J=8.8 Hz), 7.41 (d, 1H, J=8.8 Hz), 7.03 (s, 1H), 2.63 (s, 3H), 1.56 (s, 9H).

Aufarbeitung

  1. customThe solvent was removed under vacuo
  2. customThe crude product was chromatographed on silica gel
  3. washeluted with 1% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-650737852aeb440f97911a90e3517d12
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461117B2

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