Triethylamine → HCID 24876048, compound

HRID 1366235Notes

Reaction equation

HRID 1366235 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[N:8]=[C:9]3[N:13]([C:14]=2[NH:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:12]=[CH:11][S:10]3)=[N:4][CH:3]=1.[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)#[CH:21].CCN(CC)CC>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[C:16]([NH:15][C:14]1[N:13]2[C:9]([S:10][CH:11]=[CH:12]2)=[N:8][C:7]=1[C:5]1[S:6][C:2]([C:21]#[C:20][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:3][N:4]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 137268EthynylpyridineHCID 66966383HCID 66966383, compound

Product 1

HCID 24876048HCID 24876048, compoundYield 17%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 235 mg (0.66 mmol) 6-(5-bromothiazole-2-yl)-N-tert-butylimidazo[2,1-b]thiazole-5-amine, 22 mg (0.033 mmol) bis(triphenylphosphine)-palladium-(II)-chloride, 12 mg (0.066 mmol) copper-(I)-iodide, 80 μl (0.79 mmol) 2-ethynylpyridine and 731 μl (5.28 mmol) NEt3 in DMF (2 ml) was heated in the microwave (Biotage Initiator) for 10 min to 120° C. The reaction solution was diluted with water and extracted several times with AE. The collected organic phases were washed with brine and dried over MgSO4. After filtering and removal of the solvent in a vacuum, a CC (1.TBME, 2.MeOH) was performed with the residue, whereby 43 mg (0.11 mmol, 17%) N-tert-butyl-6-(5-(pyridine-2-ylethynyl)thiazole-2-yl)imidazo[2,1-b]thiazole-5-amine was obtained.

Workup

  1. temperaturewas heated in the microwave (Biotage Initiator) for 10 min to 120° C
  2. extractionextracted several times with AE
  3. washThe collected organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtering
  6. customremoval of the solvent in a vacuum

Sources & evidence

ORD record
ord-429dff4da41642afa15a15ae69f51030
Source dataset
uspto-grants-2011_02
Patent number
US07893069B2

Reaction notes

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