Potassium Carbonate → Ethyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridin-5-yl)pentanoate

HRID 2190151

Reaktionsgleichung

Reaktionsgleichung von HRID 2190151
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].B1C2CCCC1CCC2.C([O-])([O-])=O.[K+].[K+].[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:47][C:35]3=[N:36][C:37]([N:41]([CH3:46])[S:42]([CH3:45])(=[O:44])=[O:43])=[C:38](I)[CH:39]=[C:34]3[C:33]=2[C:48]([NH:50][CH3:51])=[O:49])=[CH:28][CH:27]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:47][C:35]3=[N:36][C:37]([N:41]([CH3:46])[S:42]([CH3:45])(=[O:43])=[O:44])=[C:38]([CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH:39]=[C:34]3[C:33]=2[C:48](=[O:49])[NH:50][CH3:51])=[CH:28][CH:27]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 74786Ethyl 4-pentenoateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 545750872-(4-fluorophenyl)-5-iodo-N-methyl-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridine-3-carboxamide

Produkt 1

HCID 58052319Ethyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridin-5-yl)pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 5.1 mg ethyl pent-4-enoate and 79 μl 9-BBN (2 M solution in THF) is stirred at rt for 1 h. 10 μl of water is added and stirred at rt for 10 min. 30 μl of 2 M K2CO3 solution is added and stirred at rt for 30 min. 10 mg of 2-(4-fluorophenyl)-5-iodo-N-methyl-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridine-3-carboxamide and 1.1 mg of Pd(PPh3)4 are added, bubbled with N2, and microwaved at 120 C for 20 min. The crude reaction mixture is purified with preparative HPLC to afford the title compound (M+H)+=506.3; Retention time=1.28 min, Method A.

Aufarbeitung

  1. stirringstirred at rt for 30 min
  2. custombubbled with N2
  3. custommicrowaved at 120 C for 20 min
  4. customThe crude reaction mixture
  5. customis purified with preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c102934d2736459c818ae67176197152
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324239B2

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