Triethylamine → HCID 71280782, compound

HRID 1497869Notes

Reaction equation

HRID 1497869 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([C:20]4[N:24]=[C:23]([CH:25]5[CH2:28][C:27]([F:30])([F:29])[CH2:26]5)[O:22][N:21]=4)[CH:17]=[CH:16][C:15]=3[CH3:31])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.C(N(CC)CC)C.[C:39]([Si:41]([CH3:44])([CH3:43])[CH3:42])#[CH:40]>CN(C=O)C.[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:30][C:27]1([F:29])[CH2:26][CH:25]([C:23]2[O:22][N:21]=[C:20]([C:18]3[CH:17]=[CH:16][C:15]([CH3:31])=[C:14]([NH:13][C:11]([C:8]4[N:5]5[CH:6]=[CH:7][C:2]([C:40]#[C:39][Si:41]([CH3:44])([CH3:43])[CH3:42])=[CH:3][C:4]5=[N:10][CH:9]=4)=[O:12])[CH:19]=3)[N:24]=2)[CH2:28]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 71280749HCID 71280749, compound

Product 1

HCID 71280782HCID 71280782, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

7-Bromo-N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (42f) (50.0 mg, 0.10 mmol), CuI (3.82 mg, 0.02 mmol), PdCl2(PPh3)2(14.0 mg, 0.02 mmol), triethylamine (20.0 mg, 0.20 mmol) and ethynyltrimethylsilane (20 mg, 0.20 mmol) were mixed in DMF (1 mL) in a 1 mL microwave vial. The vial was capped and heated at 110° C. for 5 minutes under microwave condition. Once complete, the reaction mixture was diluted and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered, concentrated and purified by silica chromatography to yield N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-7-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridine-3-carboxamide (52). MS m/z 506.1 (M+1)+.

Workup

  1. customThe vial was capped
  2. additionOnce complete, the reaction mixture was diluted
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica chromatography

Sources & evidence

ORD record
ord-424e26a7fdf549aebe4c61fe4181f407
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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