Potassium Carbonate → 6'-Ethynyl-2-fluoro-5-(4-piperidin-1-ylmethylphenyl)-[3,4']bipyridinyl-3'-ylamine

HRID 1888605Notes

Reaction equation

HRID 1888605 reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:14]2[C:15]([F:33])=[N:16][CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:22][CH:21]=3)[CH:19]=2)[CH:8]=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[C:6]([C:7]1[N:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:14]2[C:15]([F:33])=[N:16][CH:17]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([CH2:26][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:24][CH:25]=3)[CH:19]=2)[CH:8]=1)#[CH:5]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 582665496'-((Trimethylsilyl)ethynyl)-2-fluoro-5-(4-piperidin-1-ylmethyl-phenyl)-[3,4']bipyridinyl-3'-ylamine

Product 1

HCID 582664586'-Ethynyl-2-fluoro-5-(4-piperidin-1-ylmethylphenyl)-[3,4']bipyridinyl-3'-ylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6′-((trimethylsilyl)ethynyl)-2-fluoro-5-(4-piperidin-1-ylmethyl-phenyl)-[3,4′]bipyridinyl-3′-ylamine (90 mg, 0.2 mmol) and potassium carbonate (150 mg, 1.1 mmol) in methanol (2 mL) was stirred at ambient temperature for 1 h. The cooled reaction mixture was diluted with DCM (20 mL) and methanol (2 mL) and washed with water (15 mL). The organic phase was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford a brown residue that was taken to the next step without purification.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water (15 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a brown residue that
  8. customwas taken to the next step without purification

Sources & evidence

ORD record
ord-559c30819ed24f2aac128822fb0b8b33
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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