Triethylamine → HCID 45280537, compound

HRID 1878937Notes

Reaction equation

HRID 1878937 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:23])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])=[CH:9][CH:8]=2)=[C:4]([CH3:24])[CH:3]=1.[C:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)#[CH:26].CCN(CC)CC>C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([F:21])[C:15]=1[C:14]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[S:6][C:2]([CH2:26][CH2:25][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:3][C:4]=2[CH3:24])=[CH:8][CH:9]=1)=[O:23]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1860033-EthynylpyridineHCID 59334281HCID 59334281, compound

Product 1

HCID 45280537HCID 45280537, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-(4-(5-bromo-3-methylthiophen-2-yl)phenyl)-2,6-difluorobenzamide (a, 1 mmol), 3-ethynylpyridine (1 mmol), CuI (0.05 mmol), PdCl2(PPh3)2 (0.05 mmol) in THF (6 mL), and Et3N (3 mL) was heated in sealed tube at 100° C. for 1 h. The mixture was filtered through celite and purified by column chromatography to give a white solid (b, 46 mg).

Workup

  1. filtrationThe mixture was filtered through celite
  2. custompurified by column chromatography
  3. customto give a white solid (b, 46 mg)

Sources & evidence

ORD record
ord-49593a2da4844fcfbe9f07fb1118c614
Source dataset
uspto-grants-2012_11
Patent number
US08314130B2

Reaction notes

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