Triethylamine → 3-[4-(6-Chloro-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzoic acid

HRID 491853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491853
[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])=[N+:2]=[N-:3].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[CH:22])=[CH:17][N:16]=1.CCN(CC)CC.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.CCO.[O-]S([O-])(=O)=O.[Cu+2].C(O)(=O)C>[Cl:14][C:15]1[N:16]=[CH:17][C:18]([C:21]2[N:3]=[N:2][N:1]([C:4]3[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=3[CH3:13])[C:7]([OH:9])=[O:8])[CH:22]=2)=[CH:19][CH:20]=1

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 106542812-Chloro-5-ethynylpyridineHCID 179730913-Azido-4-methylbenzoic acidHCID 23667548Sodium Ascorbate

Produkt 1

HCID 210972923-[4-(6-Chloro-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzoic acidAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24462Copper SulfateKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

To a suspension of 308 mg (1.75 mmol) of 3-azido-4-methyl benzoic acid (U.S. Ser. No. 04/102,492) and 240 mg (1.75 mmol) of 2-chloro-5-ethynylpyridine in 1 mL of water and 2 mL of EtOH was added 243 μL (1.75 mmol) of Et3N. To this solution was added 1.75 mL of 1M aqueous sodium ascorbate followed by 1.75 mL of 0.1 M aqueous of CuSO4 and the resulting yellow suspension was stirred for two days. A 1 M solution of acetic acid in water (1.75 mL) was added along with an additional 2 mL of water. The suspension was stirred for 1 h, then was filtered, washed with water (2×2 mL) and hexanes (2×10 mL), and dried under suction to provide 470 mg of 3-[4-(6-chloro-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzoic acid.

Aufarbeitung

  1. stirringThe suspension was stirred for 1 h
  2. filtrationwas filtered
  3. washwashed with water (2×2 mL) and hexanes (2×10 mL)
  4. customdried under suction

Quellen und Nachweise

ORD-Eintrag
ord-f34c916bd597440684661e168e3eba4f
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531560B2

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