Sodium Carbonate → 4-(7-Benzenesulfonyl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1192359

Reaktionsgleichung

Reaktionsgleichung von HRID 1192359
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[C:22](Br)=[CH:21][N:20]([S:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[S:39]1[CH:43]=[CH:42][CH:41]=[C:40]1B(O)O>COCCOC.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>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[C:22]([C:40]4[S:39][CH:43]=[CH:42][CH:41]=4)=[CH:21][N:20]([S:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 675395734-(7-Benzenesulfonyl-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 675390164-(7-Benzenesulfonyl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(7-Benzenesulfonyl-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (150 mg, 0.29 mmol) in 4 mL DME (degassed with nitrogen prior to use) was added 0.94M aqueous Na2CO3 (0.61 mL, 0.57 mmol) and Pd(PPh3)4 (66 mg, 0.057 mmol). The reaction mixture was stirred 5 minutes, then 2-thiophene boronic acid (55 mg, 0.43 mmol) was added. The reaction mixture heated to reflux and stirred 16 hours, after which it was cooled to room temperature and DME was removed by rotary evaporation. The reaction mixture was diluted with H2O and extracted with DCM, and the combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was purified on silica gel (8:1 to 4:1 hexanes:EtOAc) to furnish 4-(7-Benzenesulfonyl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (120 mg, 79%) as a beige powder. LCMS (APCI+) m/z 526 [M+H]+; Rt: 3.25 min.

Aufarbeitung

  1. temperatureThe reaction mixture heated
  2. temperatureto reflux
  3. stirringstirred 16 hours
  4. customDME was removed by rotary evaporation
  5. additionThe reaction mixture was diluted with H2O
  6. extractionextracted with DCM
  7. dry with materialthe combined extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was purified on silica gel (8:1 to 4:1 hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-20f737c850e7417f949531813d893f86
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680114B2

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