Cesium carbonate → HCID 58155143, compound

HRID 1887679Notes

Reaction equation

HRID 1887679 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.Br[C:14]1[S:18][CH:17]=[N:16][C:15]=1[C:19]([NH:21][CH3:22])=[O:20].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+]>O1CCOCC1.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]>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:14]2[S:18][CH:17]=[N:16][C:15]=2[C:19]([NH:21][CH3:22])=[O:20])[C:5]([C:9]([F:10])([F:11])[F:12])=[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 58155118HCID 58155118, compoundHCID 713061562-Chloro-5-(trifluoromethyl)-4-pyridinamine

Product 1

HCID 58155143HCID 58155143, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-5-(trifluoromethyl)pyridin-4-amine (41 mg, 0.21 mmol) and 5-bromo-N-methylthiazole-4-carboxamide (54 mg, 0.24 mmol; synthesized from the corresponding ethyl-ester), Pd2(dba)3 (19 mg, 0.021 mmol), xantphos (37 mg, 0.064 mmol) and cesium carbonate (138 mg, 0.42 mmol) in dioxane (3.5 ml) were heated in a Biotage Initiator microwave synthesizer at 140° C. for 2 h. The solvent was removed and the residue was purified by silica gel chromatography (DCM/MeOH gradient) to give the title compound as a pale yellow solid in 27% isolated yield.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (DCM/MeOH gradient)

Sources & evidence

ORD record
ord-5f817b828c0649c69d337718390988f6
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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