3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → N-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-4-(5-fluoropyridin-3-yl)-3-methylthiophene-2-carboxamide

HRID 544936Notes

Reaction equation

HRID 544936 reaction equation
Br[C:2]1[C:3]([CH3:23])=[C:4]([C:7]([NH:9][C:10]2[CH:15]=[C:14]([C:16](=[O:21])[NH:17][CH:18]3[CH2:20][CH2:19]3)[CH:13]=[CH:12][C:11]=2[CH3:22])=[O:8])[S:5][CH:6]=1.[F:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=1>>[CH:18]1([NH:17][C:16]([C:14]2[CH:13]=[CH:12][C:11]([CH3:22])=[C:10]([NH:9][C:7]([C:4]3[S:5][CH:6]=[C:2]([C:29]4[CH:28]=[N:27][CH:26]=[C:25]([F:24])[CH:30]=4)[C:3]=3[CH3:23])=[O:8])[CH:15]=2)=[O:21])[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 597615124-Bromo-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-3-methylthiophene-2-carboxamide

Product 1

HCID 24985755N-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-4-(5-fluoropyridin-3-yl)-3-methylthiophene-2-carboxamide

Procedure

The title compound was prepared by coupling 4-bromo-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-3-methylthiophene-2-carboxamide with commercially available 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine using the method described in Step B of Example 136 to afford a white solid (Example 200). HPLC Ret time=2.98 min. LCMS [M+H]+ 410.22.

Workup

  1. customto afford a white solid (Example 200)
  2. customHPLC Ret time=2.98 min

Sources & evidence

ORD record
ord-59b56f6c2d4f4e8dad3096599bbcc903
Source dataset
uspto-grants-2011_05
Patent number
US07935696B2

Reaction notes

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