Triethylamine → HCID 71000688, compound

HRID 1023454Notes

Reaction equation

HRID 1023454 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:4]=1)#[CH:2].[F:13][C:14]1[CH:19]=[CH:18][C:17](I)=[C:16]([CH3:21])[CH:15]=1.C(N(CC)CC)C.[NH4+].[Cl-]>CN(C=O)C.[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2].[Cu]I.O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:4]=2)=[C:16]([CH3:21])[CH:15]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27745254-Fluoro-1-iodo-2-methylbenzeneHCID 86673609HCID 86673609, compound

Product 1

HCID 71000688HCID 71000688, compoundYield 19.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 84124Bis(triphenylphosphine)palladium chlorideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(4-Ethynyl-pyridin-2-yl)-urea (75 mg, 0.47 mmol), 4-fluoro-1-iodo-2-methyl-benzene (224 mg, 0.931 mmol), triethylamine (5.0 mL), palladium bis(triphenylphosphine)dichloride (16 mg, 0.023 mmol) and Copper (I) iodide (8.8 mg, 0.047 mmol) are mixed in DMF (1.8 mL). The reaction mixture is stirred for 16 hrs at room temperature before saturated NH4Cl solution (5 mL) is added along with water (25 mL). The mixture is extracted with EtOAc (3×20 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 5%) affords 25 mg of the desired product.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×20 mL)
  2. concentrationconcentrated
  3. customto give the crude product
  4. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-35fd92374f414824a16e4b2b340967da
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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