Potassium tert-butoxide → HCID 117815265, compound

HRID 634543Notes

Reaction equation

HRID 634543 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:13](F)=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]([S:15]CCC(OCC)=O)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]3[C:13]([S:15][C:5]2=[CH:4][CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 117815065HCID 117815065, compound

Product 1

HCID 117815265HCID 117815265, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A 500 mL RBF was charged with ethyl 3-((6-chloro-3′-fluoro-[2,2′-bipyridin]-3-yl)thio)propanoate (16.55 g, 48.6 mmol), THF (Volume: 194 mL) and degassed with nitrogen for 10 minutes, then treated with potassium 2-methylpropan-2-olate (8.17 g, 72.8 mmol) and heated to reflux at 75° C. for 24 hours. The reaction was quenched with aqueous ammonium chloride, extracted 2× with EtOAc. The crude product was purified by column chromatography to give 2-chlorothieno[3,2-b:4,5-b′]dipyridine (7 g, 68% yield).

Workup

  1. customdegassed with nitrogen for 10 minutes
  2. temperatureheated
  3. customThe reaction was quenched with aqueous ammonium chloride
  4. extractionextracted 2× with EtOAc
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-cbc788adeb9649a4aa04663cb9a9a6a7
Source dataset
uspto-grants-2016_04
Patent number
US09324949B2

Reaction notes

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