Potassium Carbonate → 6-Ethynyl-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 1888602Notes

Reaction equation

HRID 1888602 reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:15]=[CH:14][C:13]2[NH:12][C:11]3[N:16]=[CH:17][C:18]([C:20]4[CH:25]=[CH:24][C:23]([CH2:26][N:27]5[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]5)=[CH:22][CH:21]=4)=[CH:19][C:10]=3[C:9]=2[CH:8]=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[C:6]([C:7]1[N:15]=[CH:14][C:13]2[NH:12][C:11]3[N:16]=[CH:17][C:18]([C:20]4[CH:21]=[CH:22][C:23]([CH2:26][N:27]5[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]5)=[CH:24][CH:25]=4)=[CH:19][C:10]=3[C:9]=2[CH:8]=1)#[CH:5]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 582666556-((Trimethylsilyl)ethynyl)-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

Product 1

HCID 582663926-Ethynyl-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-((trimethylsilyl)ethynyl)-3-(4-piperidin-1-ylmethylphenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (120 mg, 0.3 mmol) and potassium carbonate (170 mg, 1.2 mmol) in methanol (2 mL) was stirred at ambient temperature for 1 h. The 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. washwashed with water (15 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a brown residue that
  7. customwas taken to the next step without purification

Sources & evidence

ORD record
ord-bfa60d5c4b2b47e88200d52e8ce2c0d8
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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