2-Bromothiophene → 2-Chloro-6-methyl-3-(thiophene-2-carbonyl)pyridine

HRID 1582970Notes

Reaction equation

HRID 1582970 reaction equation
[Mg].Br[C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.[Cl:8][C:9]1[N:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12]>C(OCC)C>[Cl:8][C:9]1[C:10]([C:11]([C:3]2[S:4][CH:5]=[CH:6][CH:7]=2)=[O:12])=[CH:14][CH:15]=[C:16]([CH3:18])[N:17]=1

Participants

5

Reactant 3

HCID 138512-BromothiopheneHCID 1217242-Chloro-6-methylnicotinic acidHCID 5462224Magnesium

Product 1

HCID 227167012-Chloro-6-methyl-3-(thiophene-2-carbonyl)pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a diethyl ether suspension of magnesium was added dropwise 2-bromothiophene at room temperature, and the whole was reacted. After cooling to 0° C., the reaction mixture was added with 2-chloro-6-methylnicotinic acid and, after being warmed to room temperature, the whole was stirred for 12 hours. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain 2-chloro-6-methyl-3-(thiophene-2-carbonyl)pyridine. NMR1: 7.79 (1H, dd, J=5.0, 1.1 Hz), 7.78 (1H, d, J=7.7 Hz), 2.63 (3H, s).

Workup

  1. customthe whole was reacted
  2. temperatureafter being warmed to room temperature
  3. custompurified in a usual manner

Sources & evidence

ORD record
ord-d17391885b51489b9a6a73be0ee66e39
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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