Sodium Bicarbonate → HCID 11738454, compound

HRID 1297327Notes

Reaction equation

HRID 1297327 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1B(O)O.C([O-])(O)=O.[Na+]>COCCOC.O.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>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:8]2[C:6]3=[N:7][C:2]([C:20]4[S:19][CH:23]=[CH:22][CH:21]=4)=[CH:3][N:4]=[C:5]3[N:10]=[N:9]2)=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 117383646-bromo-1-(4-fluoro-benzyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

Product 1

HCID 11738454HCID 11738454, compoundYield 18.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 6-bromo-1-(4-fluoro-benzyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (100 mg, 0.32 mmol), 2-thiopheneboronic acid (44.8 mg, 0.35 mmol), Pd(PPh3)2Cl2 (11.3 mg, 0.016 mmol), and NaHCO3 (80.6 mg, 0.96 mmol) in DME (2 mL) and water (0.4 mL) was put in a microwave reaction tube and reacted in a microwave reactor at 120° C. for 15 minutes. The reaction mixture was partitioned in ethyl acetate and water, and the organic layer was evaporated. The residue was purified on a silica gel column eluting with EtOAc-Hexane to provide 1-(4-fluoro-benzyl)-6-thiophen-2-yl-1H-[1,2,3]triazolo[4,5-b]pyrazine (18 mg).

Workup

  1. customwas put in a microwave reaction tube
  2. customreacted in a microwave reactor at 120° C. for 15 minutes
  3. customThe reaction mixture was partitioned in ethyl acetate
  4. customwater, and the organic layer was evaporated
  5. customThe residue was purified on a silica gel column
  6. washeluting with EtOAc-Hexane

Sources & evidence

ORD record
ord-945498b1681c4109a9e04746da174a0e
Source dataset
uspto-grants-2007_07
Patent number
US07250417B2

Reaction notes

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