Dimethylformamide → HCID 86712745, compound

HRID 1779118Notes

Reaction equation

HRID 1779118 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19](=[O:21])[CH3:20])=[N:17][CH:18]=2)[N:3]=1.CCN([CH2:27][CH3:28])CC.C[N:30]([CH:32]=[O:33])C>O.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.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]([C:16]1[N:17]=[CH:18][C:13]([NH:12][C:4]2[N:3]=[C:2]([C:20]#[C:19][C:16]3[CH:15]=[CH:14][CH:13]=[CH:18][C:27]=3[CH2:28][C:32]([NH2:30])=[O:33])[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[CH:14][CH:15]=1)(=[O:21])[CH3:20]

Participants

8

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 86712743HCID 86712743, compound

Product 1

HCID 86712745HCID 86712745, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

1-(5-((4-Chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)ethanone (A141) (0.313 g, 0.988 mmol) and I8 (0.189 g, 1.18 mmol) were added to a solution of PdCl2(PPh3)2 (0.017 g, 0.025 mmol), CuI (0.010 g, 0.049 mmol) and PPh3 (0.013 g, 0.049 mmol) in DMF (3 mL) and Et3N (0.552 mL, 3.95 mmol). The reaction mixture was heated under microwave irradiation at 120° C. for 15 minutes. The reaction mixture was diluted with water and then filtered. The solid was washed with water and dried before being suspended in EtOAc, ultra sonicated for 20 seconds, filtered and dried to give the title compound (A142) as a light brown solid (0.347 g, 79%). LCMS-B: rt=6.78 min; m/z=440 [M+H]+.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with water
  3. customdried
  4. customultra sonicated for 20 seconds
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-750f85c491dd40a6bc9fa33700217a5b
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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