Pyrrolidine → 5-Bromo-2-(1-pyrrolidinyl)thiazole

HRID 331036Notes

Reaction equation

HRID 331036 reaction equation
Br[C:2]1[S:3][C:4]([Br:7])=[CH:5][N:6]=1.[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.CCN(C(C)C)C(C)C>C1COCC1>[Br:7][C:4]1[S:3][C:2]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 3123942,5-Dibromothiazole

Product 1

HCID 457875555-Bromo-2-(1-pyrrolidinyl)thiazoleYield 108.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4 batches of 2,5-dibromo-1,3-thiazole (250 mg, 1.029 mmol), pyrrolidine (0.089 mL, 1.081 mmol) and DIPEA (0.225 mL, 1.286 mmol) in THF (2.5 mL) were heated in a microwave at 120° C. for 15 minutes. All 4 batches were combined and evaporated to dryness. The residues were purified on silica eluting with cyclohexane and ethyl acetate (0-100%). The appropriate fractions were combined and evaporated to dryness producing the title compound (260 mg). LCMS (A): m/z (M+H)+ 233/235, C7H9BrN2S requires 232/234 (acidic).

Workup

  1. customevaporated to dryness
  2. customThe residues were purified on silica eluting with cyclohexane and ethyl acetate (0-100%)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-0ee0ed5dac2e4811846d24eb40cab300
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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