Sodium Carbonate → Benzyl[3-(aminocarbonyl)-5-(2,4-difluorophenyl)-2-thienyl]carbamate

HRID 385695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385695
[CH2:1]([O:8][C:9](=[O:20])[NH:10][C:11]1[S:12][C:13](I)=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:20])[NH:10][C:11]1[S:12][C:13]([C:25]2[CH:24]=[CH:23][C:22]([F:21])=[CH:27][C:26]=2[F:28])=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 59525870Benzyl[3-(aminocarbonyl)-5-iodo-2-thienyl]carbamate

Produkt 1

HCID 59526381Benzyl[3-(aminocarbonyl)-5-(2,4-difluorophenyl)-2-thienyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of benzyl[3-(aminocarbonyl)-5-iodo-2-thienyl]carbamate (250 mg, 0.622 mmol), 2,4-difluorophenylboronic acid (349 mg, 2.21 mmol), dichlorobis(triphenylphosphine)palladium (21.8 mg, 0.031 mmol), and sodium carbonate (6.22 mL, 12.43 mmol) in 1,2-dimethoxyethane (10 mL) sealed in a 5 mL microwave reaction vessel was purged of oxygen by doing 5 vacuum/argon flush cycles. The reaction solution was heated in a Biotage microwave for five minutes at 100° C. The resulting mixture was partitioned between ethyl acetate (30 mL) and saturated aqueous sodium bicarbonate (20 mL). The layers were separated and the organic layer was washed with saturated sodium bicarbonate (20 mL) and brine (2×20 mL), dried over sodium sulfate, filtered, and concentrated. The crude material was purified by silica gel chromatography using a 0-4% methanol/dichloromethane elution to afford the title compound.

Aufarbeitung

  1. customsealed in a 5 mL microwave reaction vessel
  2. customwas purged of oxygen
  3. customflush cycles
  4. customThe resulting mixture was partitioned between ethyl acetate (30 mL) and saturated aqueous sodium bicarbonate (20 mL)
  5. customThe layers were separated
  6. washthe organic layer was washed with saturated sodium bicarbonate (20 mL) and brine (2×20 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was purified by silica gel chromatography
  11. washa 0-4% methanol/dichloromethane elution

Quellen und Nachweise

ORD-Eintrag
ord-b8edb81a65a14f2fa949b83f26d519d3
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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