Cesium carbonate → 1-Benzothiazol-6-yl-3-(4-methyl-pyridin-3-yl)-4-trifluoromethyl-imidazolidin-2-one

HRID 2383917Notes

Reaction equation

HRID 2383917 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH:13]([C:15]([F:18])([F:17])[F:16])[NH:12][C:11]3=[O:19])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.I[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[CH3:27].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+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH:13]([C:15]([F:17])([F:18])[F:16])[N:12]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][C:26]=4[CH3:27])[C:11]3=[O:19])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 144235133-Iodo-4-methylpyridineHCID 687879131-Benzothiazol-6-yl-4-trifluoromethyl-imidazolidin-2-one

Product 1

HCID 498725571-Benzothiazol-6-yl-3-(4-methyl-pyridin-3-yl)-4-trifluoromethyl-imidazolidin-2-oneYield 7.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Benzothiazol-6-yl-4-trifluoromethyl-imidazolidin-2-one (I-170b: 100 mg, 0.348 mmol) was reacted with 3-iodo-4-methyl-pyridine (83.9 mg, 0.383 mmol), Pd2(dba)3 (15.9 mg, 0.0174 mmol), Xantphos (30.2 mg, 0.0528 mmol), cesium carbonate (170 mg, 0.152 mmol) and 1,4-dioxane (10 mL) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in chloroform) followed by preparative HPLC afforded 10 mg of the product (7.5% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% methanol in chloroform)

Sources & evidence

ORD record
ord-6671b7b8282446be8b6a1c45a2b925d0
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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