Cesium carbonate → HCID 68407249, compound

HRID 2244427Notes

Reaction equation

HRID 2244427 reaction equation
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+].[CH2:49]([O:51][C:52]([C:54]1[N:55]=[C:56]([CH2:60][CH2:61][O:62][CH3:63])[S:57][C:58]=1[NH2:59])=[O:53])[CH3:50].Br[C:65]1[CH:66]=[N:67][CH:68]=[CH:69][CH:70]=1>O1CCOCC1.C1COCC1>[CH2:49]([O:51][C:52]([C:54]1[N:55]=[C:56]([CH2:60][CH2:61][O:62][CH3:63])[S:57][C:58]=1[NH:59][C:65]1[CH:66]=[N:67][CH:68]=[CH:69][CH:70]=1)=[O:53])[CH3:50]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68407298HCID 68407298, compound

Product 1

HCID 68407249HCID 68407249, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A microwave vial was charged with Pd2dba3-chloroform complex (0.09 g, 0.09 mmol), Xantphos (0.17 g, 0.30 mmol) and cesium carbonate (1.00 g, 3.06 mmol), sealed and flushed with argon. A solution of 5-amino-2-(2-methoxy-ethyl)-thiazole-4-carboxylic acid ethyl ester (0.40 g, 1.75 mmol) and 3-bromopyridine (0.28 g, 1.75 mmol) in dioxane (5.80 ml) was degassed by sonicating and bubbling with argon, then transferred to the reaction vial. After stirring at room temperature for 5 min, the reaction mixture was irradiated in a microwave oven at 150° C. for 10 min. The mixture was diluted with THF, filtered and the mother liquors evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate/methanol) to yield 2-(2-methoxy-ethyl)-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester (0.18 g, 40%), MS (ISP): m/e=308.3 (M+H+).

Workup

  1. customsealed
  2. customflushed with argon
  3. customby sonicating
  4. custombubbling with argon
  5. customtransferred to the reaction vial
  6. customthe reaction mixture was irradiated in a microwave oven at 150° C. for 10 min
  7. filtrationfiltered
  8. customthe mother liquors evaporated
  9. customThe residue was purified by flash chromatography (heptane/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-bd5907c7a6e148aaa427ff13e183e631
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

Loading…