N,N-Dimethylethylenediamine → HCID 67401327, compound

HRID 912895Notes

Reaction equation

HRID 912895 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17](Br)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29].C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([NH:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 67399955HCID 67399955, compound

Product 1

HCID 67401327HCID 67401327, compound

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-(5-bromo-3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester from step (b) above (174 mg, 0.42 mmol), N-(2-aminoethyl)-N,N-dimethylamine (56 μL, 0.51 mmol, Aldrich), tris (dibenzylideneacetone) dipalladium (0) chloroform adduct (22 mg, 0.021 mmol, Strem Chemicals), biphenyl-2-yl-di-tert-butyl-phosphane (13 mg, 0.042 mmol, Strem Chemicals), sodium t-butoxide (65 mg, 0.63 mmol, Aldrich) in toluene (2 mL) was subjected to microwave irradiation at 150° C. for 0.5 h. The mixture was cooled to room temperature and was filtered. The filtrate was purified by silica gel column chromatography, eluting with 5%-100% (2M NH3 in MeOH) in dichloromethane, to give the title product as a brown solid. MS (ESI, positive ion) m/z: 418 (M+1).

Workup

  1. customirradiation at 150° C. for 0.5 h
  2. filtrationwas filtered
  3. customThe filtrate was purified by silica gel column chromatography
  4. washeluting with 5%-100% (2M NH3 in MeOH) in dichloromethane

Sources & evidence

ORD record
ord-3165991c44744b8ea26fbb1179a016b3
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

Loading…