Cesium carbonate → HCID 86715113, compound

HRID 533924Notes

Reaction equation

HRID 533924 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:4][N:3]=1.[CH3:18][C:19]1[S:23][CH:22]=[N:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.CN(C=O)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:5]2[CH:6]=[CH:7][C:2]([C:22]3[S:23][C:19]([CH3:18])=[CH:20][N:21]=3)=[N:3][CH:4]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1379805-MethylthiazoleHCID 66519750HCID 66519750, compound

Product 1

HCID 86715113HCID 86715113, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture was prepared from 2-bromo-5-(4-methoxybenzyloxy)pyridine (2.0 g), 5-methylthiazole (614 mg), Pd(P(t-Bu)3)2 (253 mg), Cs2CO3 (2.02 g) and DMF (10 mL). The system was evacuated and refilled with nitrogen three times. The mixture was stirred at 150° C. under N2 atmosphere for 3 hours. After cooling, insoluble material was removed by filtration over Celite. The resulting solution was added water (100 mL). The precipitate obtained was filtered off and washed with MeOH three times to provide the subtitle compound. MS ESI+: m/z=313 [M+H]+.

Workup

  1. customThe system was evacuated
  2. additionrefilled with nitrogen three times
  3. temperatureAfter cooling
  4. custominsoluble material was removed by filtration over Celite
  5. additionThe resulting solution was added water (100 mL)
  6. customThe precipitate obtained
  7. filtrationwas filtered off
  8. washwashed with MeOH three times

Sources & evidence

ORD record
ord-831bdd17df7f46eea78a98331dda010e
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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