Dimethylformamide → tert-butyl 4-(1-{[3-(3-methoxypyrrolidin-1-yl)phenyl]sulfonyl}-1H-pyrrolo[3,2-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 641883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641883
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH:15]=2)=[CH:2]1.CN(C)C=O.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:38][O:39][CH:40]1[CH2:44][CH2:43][N:42]([C:45]2[CH:46]=[C:47]([S:51](Cl)(=[O:53])=[O:52])[CH:48]=[CH:49][CH:50]=2)[CH2:41]1>O1CCCC1>[CH3:38][O:39][CH:40]1[CH2:44][CH2:43][N:42]([C:45]2[CH:46]=[C:47]([S:51]([N:1]3[C:9]4[C:4](=[N:5][CH:6]=[CH:7][CH:8]=4)[C:3]([C:10]4[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH:15]=4)=[CH:2]3)(=[O:53])=[O:52])[CH:48]=[CH:49][CH:50]=2)[CH2:41]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 534146863-(3-Methoxy-1-pyrrolidinyl)benzenesulfonyl chlorideHCID 59259519tert-butyl 4-{1H-pyrrolo[3,2-b]pyridin-3-yl}-1,2,3,6-tetrahydropyridine-1-carboxylate

Produkt 1

HCID 59259359tert-butyl 4-(1-{[3-(3-methoxypyrrolidin-1-yl)phenyl]sulfonyl}-1H-pyrrolo[3,2-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Into a 1-Neck round-bottom flask tert-butyl 4-(1H-pyrrolo[3,2-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate (100 mg, 0.000334 mol) was stirred in tetrahydrofuran (3 mL, 0.04 mol) and N,N-dimethylformamide (3 mL, 0.04 mol) at 5° C. and 1.0 M of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.50 mL) was added. The reaction was stirred for 20 minutes at 5° C. 3-(3-Methoxypyrrolidin-1-yl)benzenesulfonyl chloride (138 mg, 0.000501 mol) in tetrahydrofuran (3 mL, 0.04 mol) was added by syringe at 5° C. and the reaction was stirred for 30 minutes. The reaction was extracted with ethyl acetate and was washed with water and brine. The solvent was rotovaped.

Aufarbeitung

  1. stirringthe reaction was stirred for 30 minutes
  2. extractionThe reaction was extracted with ethyl acetate
  3. washwas washed with water and brine

Quellen und Nachweise

ORD-Eintrag
ord-3ecbfcb2b566471eb470467e6eaacda1
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696229B2

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