Water → HCID 66775030, compound

HRID 1644173Notes

Reaction equation

HRID 1644173 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1.O.[CH:9]1([NH2:12])[CH2:11][CH2:10]1>>[CH2:10]1[CH2:11][CH:9]1[NH2:12].[Br:7][C:5]1[N:6]=[CH:2][S:3][CH:4]=1

Participants

4

Reactant 3

HCID 962WaterHCID 69828CyclopropylamineHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 66775030HCID 66775030, compound

Conditions

Temperature
50 °C

Procedure

Commercially available 2,4-dibromothiazole (2 mmol) is dissolved in cyclopropylamine (3 mL) and the reaction mixture is heated to 50° C. for 8 hour. The cooled mixture is then poured into water and extracted 2 times with ether. After drying the combined organic fractions (MgSO4), evaporation of solvents, and purification by flash column chromatography (silica gel, 15% EtOAc/Hexane) furnished 2-cyclopropylamine-4-bromothiazole which is further converted to the corresponding stannane 186f. A solution of 2-cyclopropylamine-4-bromothiazole in degassed DME is treated with hexamethylditin and Pd(PPh3)4 and heated at 80° C. for 18 hour. The cooled mixture is concentrated under vacuum and the residue is purified by column chromatography eluting with 20% EtOAc/Hexane/2% Et3N to give Stannane 186f. [M+H]+=304.1.

Workup

  1. extractionextracted 2 times with ether
  2. customAfter drying
  3. customthe combined organic fractions (MgSO4), evaporation of solvents, and purification by flash column chromatography (silica gel, 15% EtOAc/Hexane)

Sources & evidence

ORD record
ord-43b51e6c80a24ca0a878b4c0f04f5a18
Source dataset
uspto-grants-2012_02
Patent number
US08124584B2

Reaction notes

Loading…