4-Bromo-2-(fluoromethyl)thiazole → 6-Fluoro-2-(4-(2-(fluoromethyl)thiazol-4-yl)but-3-ynyl)-imidazo[1,2-a]pyridine

HRID 334784Notes

Reaction equation

HRID 334784 reaction equation
Br[C:2]1[N:3]=[C:4]([CH2:7][F:8])[S:5][CH:6]=1.[CH2:9]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]2[CH:22]=1)[CH2:10][C:11]#[CH:12]>>[F:21][C:18]1[CH:19]=[CH:20][C:15]2[N:16]([CH:22]=[C:13]([CH2:9][CH2:10][C:11]#[C:12][C:2]3[N:3]=[C:4]([CH2:7][F:8])[S:5][CH:6]=3)[N:14]=2)[CH:17]=1

Participants

3

Reactant 2

HCID 187616114-Bromo-2-(fluoromethyl)thiazoleHCID 860867362-(But-3-ynyl)-6-fluoro-imidazo[1,2-a]pyridine2×

Product 1

HCID 665980516-Fluoro-2-(4-(2-(fluoromethyl)thiazol-4-yl)but-3-ynyl)-imidazo[1,2-a]pyridineYield 49.8%

Procedure

The title compound was prepared in accordance with the general method of Example 190(F), from 4-bromo-2-(fluoromethyl)thiazole (84 mg, 0.43 mmol) and 2-(but-3-ynyl)-6-fluoro-imidazo[1,2-a]pyridine (compound 223(E), 80 mg, 0.43 mmol). The crude residue was purified over C18 chromatography (prepacked 35 g silicagel column, H2O/CH3CN: from 100/0 to 80/20 as eluent) to afford 65 mg of 6-fluoro-2-(4-(2-(fluoromethyl)thiazol-4-yl)but-3-ynyl)-imidazo[1,2-a]pyridine (Yield: 47%) as a beige powder (Mp=82-84° C.).

Workup

  1. customThe crude residue was purified over C18 chromatography (prepacked 35 g silicagel column, H2O/CH3CN: from 100/0 to 80/20 as eluent)

Sources & evidence

ORD record
ord-1a4e406ec30d4c958e114701f1be97a6
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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