Ethyl Acetate → 3,5-Dichloro-N-(6-chloro-4-o-tolyl-pyridin-3-yl)-N-methyl-benzamide

HRID 877971Notes

Reaction equation

HRID 877971 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5](Cl)=[O:6].[Cl:12][C:13]1[N:18]=[CH:17][C:16]([NH:19][CH3:20])=[C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH:14]=1.CCN(C(C)C)C(C)C.CCOC(C)=O>C(Cl)Cl.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([N:19]([C:16]1[CH:17]=[N:18][C:13]([Cl:12])=[CH:14][C:15]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27])[CH3:20])=[O:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 761913,5-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 577104436-chloro-N-methyl-4-(2-methylphenyl)pyridin-3-amine

Product 1

HCID 601971903,5-Dichloro-N-(6-chloro-4-o-tolyl-pyridin-3-yl)-N-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

3,5-Dichlorobenzoyl chloride (635 mg, 3.03 mmol, CAS RN 2905-62-6) was added to a solution of 6-chloro-N-methyl-4-o-tolylpyridin-3-amine (470 mg, 2.02 mmol, prepared as described in WO2005/002577) and DIPEA (705 μL, 4.04 mmol) in CH2Cl2 (15 mL). The reaction mixture was stirred for 1 h after which the reaction mixture was loaded directly onto a silica gel column. The title compound was isolated by flash chromatography (25% EtOAc in n-hexane) as a foamy oil (641 mg, 78%). MS (ESI): m/z=404.9 [M+H]+.

Sources & evidence

ORD record
ord-5126d75c00a54cf195008eafeaf5deed
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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