Diisopropylethylamine → Ethyl 1-(2-fluorobenzyl)-5-{[(2methyl-1,3-dioxolan-2-yl)acetyl]amino}-1H-indole-2-carboxylate

HRID 1824984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1824984
[CH3:1][C:2]1([CH2:7][C:8]([OH:10])=O)[O:6][CH2:5][CH2:4][O:3]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:44][C:45]1[CH:46]=[C:47]2[C:51](=[CH:52][CH:53]=1)[N:50]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[F:61])[C:49]([C:62]([O:64][CH2:65][CH3:66])=[O:63])=[CH:48]2>CN(C=O)C>[F:61][C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=1[CH2:54][N:50]1[C:51]2[C:47](=[CH:46][C:45]([NH:44][C:8](=[O:10])[CH2:7][C:2]3([CH3:1])[O:3][CH2:4][CH2:5][O:6]3)=[CH:53][CH:52]=2)[CH:48]=[C:49]1[C:62]([O:64][CH2:65][CH3:66])=[O:63]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 5600442-(2-Methyl-1,3-dioxolan-2-yl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22144678Ethyl 5-amino-1-(2-fluorobenzyl)-1H-indole-2-carboxylate

Produkt 1

HCID 22144636Ethyl 1-(2-fluorobenzyl)-5-{[(2methyl-1,3-dioxolan-2-yl)acetyl]amino}-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

140 mg (0.96 mmol) of (2-methyl-1,3-dioxolan-2-yl)acetic acid are added to 5 ml of DMF, and 547 mg (1.44 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate and 186 mg (0.25 ml, 1.44 mmol) of N,N-diisopropylethylamine are added. 300 mg (0.96 mmol) of ethyl 5-amino-1-(2-fluorobenzyl)-1H-indole-2-carboxylate from Example XXXVI are added. The mixture is stirred at RT for 3 hours. For work-up the DMF is removed using a rotary evaporator. The residue is taken up in dichloromethane and extracted with aqueous hydrochloric acid. The organic phase is dried with sodium sulphate, filtered and dried under reduced pressure.

Aufarbeitung

  1. additionare added
  2. customFor work-up the DMF is removed
  3. customa rotary evaporator
  4. extractionextracted with aqueous hydrochloric acid
  5. dry with materialThe organic phase is dried with sodium sulphate
  6. filtrationfiltered
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-66866c5bd248492c9c710ac4c4fe79d8
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045544B2

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