Methyl 4-(bromomethyl)benzoate → HCID 58614817, compound

HRID 923033Notes

Reaction equation

HRID 923033 reaction equation
BrCC1C=CC(C(OC)=O)=CC=1.[CH3:13][S:14]([CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=O)=[CH:20][CH:19]=1)(=[O:16])=[O:15].[Cl:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][C:30]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.CS(CC1C=CC(C(O)=O)=CC=1)(=O)=O>>[Cl:28][C:29]1[CH:35]=[CH:34][C:32]([NH:33][C:22](=[O:24])[C:21]2[CH:20]=[CH:19][C:18]([CH2:17][S:14]([CH3:13])(=[O:15])=[O:16])=[CH:27][CH:26]=2)=[CH:31][C:30]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1

Participants

5

Reactant 4

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 5060694-(MethanesulfonylMethyl)benzoic acidHCID 2804364methyl 4-(methylsulfonylmethyl)benzoateHCID 401519254-Chloro-3-(pyridin-2-yl)aniline

Product 1

HCID 58614817HCID 58614817, compound

Procedure

1 g of methyl 4-(bromomethyl)benzoate was reacted via Procedure O. 2.77 g of methyl 4-(methylsulfonylmethyl)benzoate was hydrolyzed via Procedure M. 1 g of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 1.15 g of 4-(methylsulfonylmethyl)benzoic acid via Procedure G. The crude product was subjected to basic workup and recrystallized with 1:1 Ratio of Isopropylacetate and Ether to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonylmethyl)benzamide. MS (Q1) 401 (M)+.

Workup

  1. customrecrystallized with 1:1 Ratio of Isopropylacetate and Ether

Sources & evidence

ORD record
ord-3b795d29774a43ef9a6d3e33ce14de7c
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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