2-Amino-3-benzyloxypyridine → 8-(Benzyloxy)-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridine

HRID 334787Notes

Reaction equation

HRID 334787 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][C:18](=O)[CH2:19][CH2:20][C:21]#[C:22][Si:23]([CH3:26])([CH3:25])[CH3:24]>>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([CH:17]=[C:18]([CH2:19][CH2:20][C:21]#[C:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[N:15]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 903342-Amino-3-benzyloxypyridineHCID 860867691-Bromo-6-(trimethylsilyl)hex-5-yn-2-one2×

Product 1

HCID 665983368-(Benzyloxy)-2-(4-(trimethylsilyl)but-3-ynyl)-imidazo[1,2-a]pyridine

Procedure

The title compound was prepared in accordance with the general method of Example 223(D), from 3-(benzyloxy)pyridin-2-amine (274 mg, 1.37 mmol) and 1-bromo-6-(trimethylsilyl)hex-5-yn-2-one (compound 223(C), 750 mg, 3.0 mmol). The crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH: from 98/2 to 95/5 as eluent) to afford 331 mg of 8-(benzyloxy)-2-(4-(trimethylsilyl)but-3-ynyl)H-imidazo[1,2-a]pyridine (Yield: 69%) as a yellow oil.

Workup

  1. customThe crude residue was purified over silicagel chromatography (prepacked 25 g silicagel column, DCM/MeOH: from 98/2 to 95/5 as eluent)

Sources & evidence

ORD record
ord-377f1f4310ec4c61b1c9b0322bcc7fe6
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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