Potassium Carbonate → HCID 59835733, compound

HRID 1916655Notes

Reaction equation

HRID 1916655 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([O:24][CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[C:20]([CH:23]=3)[CH:21]=O)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:32]([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([O:24][CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][CH2:30][CH2:31]4)=[C:20]([C:21]#[CH:32])[CH:23]=3)=[N:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59835895HCID 59835895, compound

Product 1

HCID 59835733HCID 59835733, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

152 mg (0.79 mmol) dimethyl (1-diazo-2-oxo-propyl)-phosphate in 2 mL MeOH are added to a solution of 300 mg (0.66 mmol) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde (Example 3.55b) and 183 mg (1.32 mmol) K2CO3 in 9 mL MeOH. The reaction solution is stirred for for 3 h at RT and diluted with 20 mL DCM. The organic phase is extracted twice with saturated NaHCO3 solution. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by HPLC-MS.

Workup

  1. extractionThe organic phase is extracted twice with saturated NaHCO3 solution
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe purification

Sources & evidence

ORD record
ord-b61ea3cc4b1546df8a1b7f8383f7f69d
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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