4-Fluorobenzaldehyde → HCID 178505538, compound

HRID 2264206Notes

Reaction equation

HRID 2264206 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][C:10]([NH2:19])=[C:9]([NH2:20])[N:8]=2)[CH:2]=1.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1>O1CCOCC1>[F:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]2[NH:20][C:9]3=[N:8][C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[C:12]([C:13]4[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=4)[CH:11]=[C:10]3[N:19]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 59595958HCID 59595958, compound

Product 1

HCID 178505538HCID 178505538, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A sealed tube containing 3,2′:3′,4″-terpyridine-5′,6′-diamine (Intermediate 2,148 mg, 0.56 mmol), 4-fluorobenzaldehyde (57.0 μL, 0.53 mmol) and dioxane (3 mL) was filled with air and heated to 100° C. for 6 days. Then, the solvent was removed and CH3CN (2 mL) followed by Yb(OTf)3 were added, and the reaction mixture was stirred for 4 days at room temperature. Afterwards, the solvent was evaporated in vacuo and the residue was purified by flash column chromatography (CH2Cl2/EtOH/aq NH3 100:8:1) to afford the title compound as a white solid (27 mg, 13%).

Workup

  1. additionwas filled with air
  2. customThen, the solvent was removed
  3. additionwere added
  4. customAfterwards, the solvent was evaporated in vacuo
  5. customthe residue was purified by flash column chromatography (CH2Cl2/EtOH/aq NH3 100:8:1)

Sources & evidence

ORD record
ord-47deb04d621c4c32a20da7d15b9ff33d
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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