2-Bromothiazole → HCID 70980091, compound

HRID 1475428Notes

Reaction equation

HRID 1475428 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Mg]Cl)(C)C.[Li+].[Cl-].[C:14]([O:18][C:19]([N:21]1[CH2:26][C@@H:25]([CH3:27])[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23][C@@H:22]1[CH:35]=[O:36])=[O:20])([CH3:17])([CH3:16])[CH3:15]>C1COCC1>[C:14]([O:18][C:19]([N:21]1[CH2:26][C@@H:25]([CH3:27])[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23][C@@H:22]1[CH:35]([OH:36])[C:2]1[S:3][CH:4]=[CH:5][N:6]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 764302-BromothiazoleHCID 433294Lithium ChlorideHCID 86724016HCID 86724016, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 70980091HCID 70980091, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4 °C

Procedure

2-Bromothiazole (0.500 g, 3.05 mmol) was dissolved in anhydrous THF (7.62 mL) and cooled to 4° C. (ice bath) under nitrogen. i-PrMgCl.LiCl in THF (2.0 M, 1.52 mL, 3.05 mmol) was added and the reaction stirred at this temperature for 30 minutes. The ice bath was removed and the reaction stirred for 30 minutes at room temperature. (2R,5R)-2-Formyl-5-methyl-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.500 g, 1.52 mmol) was added and the reaction stirred for 2 h. The reaction mixture was quenched with water and extracted with DCM (3×). The combined organic extracts were dried with sodium sulfate, filtered and concentrated. Chromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60) gave the title compound (473 mg). MS: [M+H]+=414.

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction stirred for 30 minutes at room temperature
  3. stirringthe reaction stirred for 2 h
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with DCM (3×)
  6. dry with materialThe combined organic extracts were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washChromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60)

Sources & evidence

ORD record
ord-136ec6612238446aa41598375f74066c
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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