Nitrogen → HCID 25216554, compound

HRID 910680Notes

Reaction equation

HRID 910680 reaction equation
N#N.[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[CH:17]=[C:18](OS(C(F)(F)F)(=O)=O)[CH:19]=[CH:20][CH:21]=3)[CH:11]=2)[CH2:6][CH2:5]1.[F:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1.CCO>[F:30][C:31]1[CH:36]=[CH:35][C:34]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:12]3[CH:11]=[C:10]([N:7]4[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]4)[CH:15]=[CH:14][N:13]=3)[CH:17]=2)=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86628635HCID 86628635, compound

Product 1

HCID 25216554HCID 25216554, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a N2 flushed vial was sequentially added trifluoromethanesulfonic acid 3-[4-(4-methyl-piperazin-1-yl)-pyridin-2-yl]-phenyl ester (20 mg, 0.05 mmol), Pd(PPh3)4 (10 mg), and toluene/EtOH (4:1, 1 mL). After 5 min, 4-fluorophenylboronic acid (10 mg, 0.07 mmol) and 2 M aqueous K2CO3 (0.2 mL) were added. The resulting mixture was heated at 90° C. for 16 h, then was poured into water and extracted with CH2Cl2. The organic layer was dried and concentrated, and the resulting residue was purified by preparative TLC (MeOH/CH2Cl2) to yield the title compound as a solid.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe resulting residue was purified by preparative TLC (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-82c0f97a9a024d3984cda4fc7b4ee291
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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