Triethylamine → N-tert-butyl-6-(5-((3-fluoropyridine-2-yl)ethynyl)thiophene-2-yl)imidazo[2,1-b]thiazole-5-amine

HRID 1366240Notes

Reaction equation

HRID 1366240 reaction equation
[C:1]([NH:5][C:6]1[N:13]2[C:9]([S:10][CH:11]=[CH:12]2)=[N:8][C:7]=1[C:14]1[S:15][C:16]([C:19]#[CH:20])=[CH:17][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[F:21][C:22]1[C:23](I)=[N:24][CH:25]=[CH:26][CH:27]=1.CCN(CC)CC>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:1]([NH:5][C:6]1[N:13]2[C:9]([S:10][CH:11]=[CH:12]2)=[N:8][C:7]=1[C:14]1[S:15][C:16]([C:19]#[C:20][C:23]2[C:22]([F:21])=[CH:27][CH:26]=[CH:25][N:24]=2)=[CH:17][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15194833-Fluoro-2-iodopyridineHCID 86625957N-tert-butyl-6-(5-ethynylthiophene-2-yl)imidazo[2,1-b]thiazole-5-amine

Product 1

HCID 24876138N-tert-butyl-6-(5-((3-fluoropyridine-2-yl)ethynyl)thiophene-2-yl)imidazo[2,1-b]thiazole-5-amineYield 77.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Procedure

A solution of 450 mg (1.49 mmol) N-tert-butyl-6-(5-ethynylthiophene-2-yl)imidazo[2,1-b]thiazole-5-amine, 333 mg (1.90 mmol) 3-fluoro-2-iodo-pyridine, 38 mg (0.06 mmol) bis(triphenylphosphine)-palladium-(II)-chloride, 19 mg (0.07 mmol) copper-(I)-iodide and 389 μl (2.80 mmol) NEt3 in AE (21 ml) was heated to 50° C. while being stirred for 20 h. Concentration in a vacuum was subsequently performed and a CC (AE) carried out with the residue, whereby 456 mg (1.15 mmol, 77%) N-tert-butyl-6-(5-((3-fluoropyridine-2-yl)ethynyl)thiophene-2-yl)imidazo[2,1-b]thiazole-5-amine was obtained.

Workup

  1. concentrationConcentration in a vacuum

Sources & evidence

ORD record
ord-c7152efbdece49cfad64e5844e2a6359
Source dataset
uspto-grants-2011_02
Patent number
US07893069B2

Reaction notes

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