2-Amino-6-methylpyridine → 2-Bromo-5-methyl-thiophene-3-carboxylic acid (6-methyl-pyridin-2-yl)-amide

HRID 2244411Notes

Reaction equation

HRID 2244411 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH3:7])=N[C:3]=1[C:8]([OH:10])=O.[CH3:11]CN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:42][C:43]1[N:48]=[C:47]([NH2:49])[CH:46]=[CH:45][CH:44]=1>CN(C)C=O>[CH3:42][C:43]1[N:48]=[C:47]([NH:49][C:8]([C:3]2[CH:11]=[C:5]([CH3:7])[S:6][C:2]=2[Br:1])=[O:10])[CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 157652-Amino-6-methylpyridineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 451175845-Bromo-2-methyl-1,3-thiazole-4-carboxylic acid

Product 1

HCID 866065662-Bromo-5-methyl-thiophene-3-carboxylic acid (6-methyl-pyridin-2-yl)-amideYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-2-methyl-thiazole-4-carboxylic acid (prepared as described in example 119, steps A to B) (0.31 g, 1.39 mmol) in dimethylformamide (20.00 ml) was treated with DIPEA (0.27 g, 2.08 mmol), TBTU (0.47 g, 1.46 mmol) and 6-methyl-pyridin-2-ylamine (0.18 g, 1.66 mmol) and stirred at room temperature overnight. The volatiles were removed under vacuum and the residue purified by flash chromatography (heptane/ethyl acetate) to yield 2-bromo-5-methyl-thiophene-3-carboxylic acid (6-methyl-pyridin-2-yl)-amide (0.16 g, 38%) as a light yellow solid, MS (ISP): m/e=314.0, 312.0 (M+H+)

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe residue purified by flash chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-22bba7c22a714ca3870d1ca8504c2343
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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