Dichloromethane → N-(2-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)propan-2-yl)ethanesulfonamide

HRID 391307Notes

Reaction equation

HRID 391307 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])([CH3:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.[Cl:17][C:18]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[CH:22][C:19]=1[C:20]#[N:21].C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:17][C:18]1[CH:25]=[C:24]([C:2]2[CH:3]=[C:4]([C:8]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])([CH3:10])[CH3:9])[CH:5]=[N:6][CH:7]=2)[CH:23]=[CH:22][C:19]=1[C:20]#[N:21]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 579261132-Chloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 59578400N-(2-(5-bromopyridin-3-yl)propan-2-yl)ethanesulfonamide

Product 1

HCID 49820278N-(2-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)propan-2-yl)ethanesulfonamideYield 2.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(2-(5-bromopyridin-3-yl)propan-2-yl)ethanesulfonamide (30 mg, 0.098 mmol), 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (27.0 mg, 0.103 mmol), PdCl2(dppf).CH2Cl2 adduct (1.994 mg, 2.441 μmol) and sodium carbonate (98 μl, 0.195 mmol) in DMF (10 mL) was heated to 100° C. overnight. After concentration, the residue was purified by column (MeOH—CH2Cl2, v/v, 10-20%) yielded the title compound as oil (1 mg). ESI-MS m/z: [M+1]+364.0, Retention time=1.40 min. 1H NMR (400 MHz, CDCl3): δ 1.31 (t, J=7.37 Hz, 3H), 1.76 (s, 6H), 2.86-2.91 (m, 21-1), 4.54 (brs, 1H), 7.52 (dd, J=1.7, 8 Hz, 1H), 7.67 (d, J=1.6 Hz, 1H), 7.72 (d, J=8 Hz, 1H), 7.95 (t, J=2.2 Hz, 1H), 8.67 (d, J=2.2 Hz, 1H), 8.76 (d, J=2.2 Hz, 1H).

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by column (MeOH—CH2Cl2, v/v, 10-20%)

Sources & evidence

ORD record
ord-6060b30a7fbe47ec8c959d94aed66043
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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