Triethylamine → 5-Bromo-6-cyclopropyl-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 531446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 531446
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:11])=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.C(N(CC)CC)C.[C:20]([Si:22]([CH3:25])([CH3:24])[CH3:23])#[CH:21]>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.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:21]#[C:20][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:5]([NH2:11])=[N:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 900227685-Bromo-6-cyclopropyl-3-iodopyridin-2-amine

Produkt 1

HCID 900223295-Bromo-6-cyclopropyl-3-((trimethylsilyl)ethynyl)pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Cuprous iodide (11.23 mg, 0.059 mmol) was added to a mixture of 5-bromo-6-cyclopropyl-3-iodopyridin-2-amine (1 g, 2.95 mmol), triethylamine (13.4 g, 132.75 mmol) and THF (4 mL) and the resultant mixture was purged with nitrogen gas. Ethynyltrimethylsilane (347.7 mg, 3.54 mmol) and Pd(PPh3)2Cl2 (41.36 mg, 0.059 mmol) were added and purged with argon. The resultant mixture was stirred under argon atmosphere for 5 hours. The mixture was concentrated to residue. Residue was dissolved in ethyl acetate, washed with water, brine and dried over sodium sulfate and concentrated to get solid which was further purified on column (SiO2) using 15% ethyl acetate in hexane as eluent. This afforded 1.2 g (crude) of the pure compound.

Aufarbeitung

  1. customthe resultant mixture was purged with nitrogen gas
  2. custompurged with argon
  3. concentrationThe mixture was concentrated to residue
  4. dissolutionResidue was dissolved in ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto get solid which
  9. customwas further purified on column (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-c6a1cba5708f4403b9ead3e340915243
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353107B2

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