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4-Chloroaniline → HCID 25230563, compound

HRID 1961716
Notes
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Reaction equation

HRID 1961716 reaction equation
Cl[C:2]1[C:3]([CH2:15][O:16][CH3:17])=[N:4][CH:5]=[C:6]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[N:9]2)[N:7]=1.[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:2]2[C:3]([CH2:15][O:16][CH3:17])=[N:4][CH:5]=[C:6]([N:8]3[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[N:9]3)[N:7]=2)=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 78124-ChloroanilineHCID 10796Cesium carbonateHCID 59570670HCID 59570670, compound

Product 1

HCID 25230563HCID 25230563, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst
HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-chloro-5-(3,5-dimethyl-pyrazol-1-yl)-2-methoxymethyl-pyrazine (34 mg, 0.12 mmol), 4-chloroaniline (22 mg, 0.17 mmol) and cesium carbonate (80 mg, 0.24 mmol) in dry dioxane (2 mL) was degassed with argon for 15 minutes. Tris(dibenzylideneacetone)dipalladium (0) (3 mg, 0.003 mmol) and 1,1′-bis(diphenyl-phosphino) ferrocene (6 mg, 0.01 mmol) were added followed by degassing for 5 minutes and the reaction mixture was stirred at 120° C. over night. Dichloromethane was added and the solution was filtrated. The filtrate was concentrated in vacuo. Flash chromatography (ethyl acetate/heptane as eluent) gave (4-chloro-phenyl)-[6-(3,5-dimethyl-pyrazol-1-yl)-3-methoxymethyl-pyrazin-2-yl]-amine (33 mg, 80%) as a white solid.

Workup

  1. customwas degassed with argon for 15 minutes
  2. customby degassing for 5 minutes
  3. additionDichloromethane was added
  4. filtrationthe solution was filtrated
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bf649b410e994cdc9beb3e70cb29dbce
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415358B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes