Potassium Carbonate → HCID 71212573, compound

HRID 513186Notes

Reaction equation

HRID 513186 reaction equation
Br[C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.Cl.[CH3:9][CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:7][C:4]1[S:3][C:2]([N:12]2[CH2:13][CH2:14][CH:10]([CH3:9])[CH2:11]2)=[N:6][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3123942,5-DibromothiazoleHCID 124643143-Methylpyrrolidine--hydrogen chloride (1/1)

Product 1

HCID 71212573HCID 71212573, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2,5-Dibromothiazole (250 mg, 1.029 mmole), 3-methyl-pyrrolidine hydrochloride (188 mg, 1.544 mmole), and K2CO3 (569 mg, 4.12 mmole) were combined in DMF (5 mL) then heated to 100° C. After stirring overnight the mixture was cooled to RT, diluted with H2O and extracted with EtOAc (3×). The combined organic layers were washed with H2O and brine, dried (MgSO4), filtered, and concentrated. Flash column chromatography (Biotage-SNAP-10 g SiO2, 0-50% EtOAc/hexanes) gave the title compound (234 mg, 92%) as a pale yellow oil. 1H NMR (399 MHz, CDCl3): δ 7.06 (s, 1 H); 3.58-3.45 (m, 2 H); 3.45-3.35 (m, 1 II); 2.97 (dd, J=9.7, 7.7 Hz, 1 H); 2.47-2.36 (m, 1 H); 2.20-2.10 (m, 1 H); 1.73-1.63 (m, 1 H); 1.12 (d, J=6.7 Hz, 3H).

Workup

  1. temperaturewas cooled to RT
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61ea1cea5c5240718fac87406668c620
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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