Triethylamine → N-(5-iodo-6-methylpyridin-3-yl)-3-(trifluoromethyl)benzamide

HRID 1894905Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[N:6][C:7]=1[CH3:8].C(N(CC)CC)C.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](Cl)=[O:23]>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][CH:27]=[C:19]([C:18]([F:17])([F:28])[F:29])[CH:20]=2)[CH:5]=[N:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-iodo-6-methylpyridin-3-amine (125 mg, 0.534 mmol) in methylene chloride (1 mL) was added triethylamine (0.087 mL, 0.627 mmol) and cooled at 0° C. Into the reaction was added 3-(trifluoromethyl)benzoyl chloride (0.0812 mL, 0.538 mmol) dropwise and stirred at 0° C. for 45 minutes and at 25° C. for 16 hours. The reaction was extracted with EtOAc and the organic extracts were washed with water saturated Na2CO3, saturated NaCl, dried (MgSO4) and stripped in vacuo. The product was used in the next reaction without purification.

Workup

extractionThe reaction was extracted with EtOAc
washthe organic extracts were washed with water saturated Na2CO3, saturated NaCl
dry with materialdried (MgSO4)
customThe product was used in the next reaction without purification

Sources & evidence

ORD record: ord-fdd556997cbd490fa4e181c61ae4a092
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513270B2

Reaction notes

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