4-Chloroaniline → HCID 25230563, compound

HRID 1961716Notes

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

Participants

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

customwas degassed with argon for 15 minutes
customby degassing for 5 minutes
additionDichloromethane was added
filtrationthe solution was filtrated
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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