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Sodium Carbonate → 6-methoxy-3-methyl-2-trimethylsilanyl-1H-indole-5-carboxylic acid methyl ester

HRID 76093
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 76093
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8](Br)[C:7]([NH2:11])=[CH:6][C:5]=1[O:12][CH3:13].[CH3:15][Si:16]([CH3:21])([CH3:20])[C:17]#[C:18][CH3:19].C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][C:5]=1[O:12][CH3:13])[NH:11][C:17]([Si:16]([CH3:21])([CH3:20])[CH3:15])=[C:18]2[CH3:19])=[O:14]
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Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 803631-(Trimethylsilyl)prop-1-yneHCID 2768028Methyl 4-amino-5-bromo-2-methoxybenzoate

Produkt 1

HCID 585801276-methoxy-3-methyl-2-trimethylsilanyl-1H-indole-5-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553
Tetrabutylammonium Iodide
Katalysator
HCID 167845palladium(II) acetateKatalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

An indole hydrazide can also be prepared by treating a solution of 2-methoxy-4-amino-benzoic acid methyl ester (xvii) in ethanol with N-bromosuccinamide to form 2-methoxy-4-amino-5-bromo-benzoic acid methyl ester (xviii) (see Scheme VIII). A solution of 2-methoxy-4-amino-5-bromo-benzoic acid methyl ester (xviii) in DMF is then reacted with trimethyl-prop-1-ynyl silane (xix) in the presence of with palladium acetate, Na2CO3, triphenylphosphine and tetrabutylaminium iodide to form 6-methoxy-3-methyl-2-trimethylsilanyl-1H-indole-5-carboxylic acid methyl ester (xx). Compound (xx) is then treated with an aqueous HCl solution to remove the trimethylsilanyl group and form 6-methoxy-3-methyl-1H-indole-5-carboxylic acid methyl ester (xxi). Compound (xxi) is treated with NaOH in a THF/H2O solution to convert the ester to a carboxylic acid. The carboxylic acid is then activated by treating it with oxalyl chloride in dichloromethane and a catalytic amount of DMF, then the activated carboxylic acid is converted to a hydrazide by treating it with hydrazine hydrate in dichloromethane to form 6-methoxy-3-methyl-1H-indole-5-carboxylic acid hydrazide (xxii). Hydrazide (xxii) can be used in the method of Scheme Vor VI to form a compound of the invention

Quellen und Nachweise

ORD-Eintrag
ord-a2e1c695081f47fa8eee980de04ec85d
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08835464B2

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