1-Methylpiperazine → HCID 57659326, compound

HRID 2383007Notes

Reaction equation

HRID 2383007 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[CH:10][C:11]=2[C:12](N)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([C:40]2[CH:45]=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC([O-:50])(C)C.[Na+].[CH3:52][N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH2:45]([O:13][C:12]([C:11]1[CH:10]=[C:9]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[NH:8][C:7]=1[C:1]1[CH:6]=[CH:5][C:4]([N:56]2[CH2:57][CH2:58][N:53]([CH3:52])[CH2:54][CH2:55]2)=[CH:3][CH:2]=1)=[O:50])[CH3:40]

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 16747641HCID 16747641, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 57659326HCID 57659326, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ester 50 (30 mg, 0.08 mmol, obtained as described in Example 1), Pd(OAc)2 (1 mg, 0.0045 mmol), (2-biphenylyl)dicyclohexylphosphine (3 mg, 0.008 mmol), tBuONa (16 mg, 0.17 mmol), 1-methylpiperazine (60 μL, 0.54 mmol), in toluene (1 mL) and anhydrous DMF (0.2 mL) was subdued to the action of microwaves at 130° C. for 20 min. After filtration on celite and aqueous work-up (EtOAc/water) the crude 2-[4-(4-methyl-piperazin-1-yl)-phenyl]-5-pyridin-4-yl-1H-pyrrole-3-carboxylic acid ethyl ester was obtained.

Workup

  1. filtrationAfter filtration on celite and aqueous work-up (EtOAc/water) the crude 2-[4-(4-methyl-piperazin-1-yl)-phenyl]-5-pyridin-4-yl-1H-pyrrole-3-carboxylic acid ethyl ester
  2. customwas obtained

Sources & evidence

ORD record
ord-4cec8af1ebd44560baa6b6b2feb66d3b
Source dataset
uspto-grants-2012_09
Patent number
US08263604B2

Reaction notes

Loading…