4-Chloro-3-(pyridin-2-yl)aniline → HCID 58614661, compound

HRID 1364877Notes

Reaction equation

HRID 1364877 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[CH2:15]([S:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[C:22]([CH3:29])[CH:21]=1)(=[O:19])=[O:18])[CH3:16]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:20]([S:17]([CH2:15][CH3:16])(=[O:19])=[O:18])=[CH:21][C:22]=2[CH3:29])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 66878344HCID 66878344, compound

Product 1

HCID 58614661HCID 58614661, compound

Procedure

4 g of 4-bromo-2-methylbenzonitrile was used in Procedure Q with ethanethiol to afford 4-(ethylthio)-2-methylbenzonitrile. 2 g of 4-(ethylthio)-2-methylbenzonitrile was reacted via Procedure R to give 4-(ethylsulfonyl)-2-methylbenzonitrile. 2.5 g of 4-(ethylsulfonyl)-2-methylbenzonitrile was reacted via Procedure T to give 4-(ethylsulfonyl)-2-methylbenzoic acid. 75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 4-(ethylsulfonyl)-2-methylbenzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(ethylsulfonyl)-2-methylbenzamide. MS (Q1) 415.0 (M)+.

Workup

  1. customThe product was purified on reverse phase HPLC

Sources & evidence

ORD record
ord-4953ec3e3a6e48db96b5fb0cdb887098
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

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