Cesium carbonate → HCID 86668813, compound

HRID 921392Notes

Reaction equation

HRID 921392 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5](C)=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 126463662-(Propane-2-sulfonyl)anilineHCID 454803272-Chloro-4-iodo-5-methylpyridine

Product 1

HCID 86668813HCID 86668813, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-chloro-4-iodo-5-methylpyridine (2.00 mmol) in 8 mL toluene is added 1-amino-2-(isopropylsulphonyl)benzene (2.20 mmol), palladium acetate (22.4 mg, 0.0100 mmol), XANTPHOS (69.4 mg, 0.120 mmol), and cesium carbonate (2.20 mmol). The mixture is purged with nitrogen, and can be subjected to microwaves at 100° C. until formation of 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyridin-4-amine. The reaction mixture can then be concentrated and purified by silica gel chromatography.

Workup

  1. customThe mixture is purged with nitrogen
  2. customcan be subjected to microwaves at 100° C. until formation of 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyridin-4-amine
  3. concentrationThe reaction mixture can then be concentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-7fcbb500c6f64beeb11e2a71ae7b6a1e
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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