3-Bromopyridine → HCID 56942896, compound

HRID 1843936Notes

Reaction equation

HRID 1843936 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:9]=2)[C:4](=[O:16])[NH:3]1.Br[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.O1CCOCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CCCCCC.[Cu](I)I.C(OC(=O)C)C>[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([C:12]([F:13])([F:15])[F:14])=[CH:8][CH:9]=2)[C:4](=[O:16])[N:3]1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 122863-BromopyridineHCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 66801674HCID 66801674, compound

Product 1

HCID 56942896HCID 56942896, compoundYield 61.8%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one (I-43d: 40 mg, 0.1745 mmol) was reacted with 3-bromo-pyridine (19 mg, 0.1163 mmol), 1,4-dioxane (5 mL), copper iodide (4 mg), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (8 mg) and potassium phosphate (93 mg, 0.4363 mmol). The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mass was concentrated under reduced pressure and partitioned between ethylacetate and water. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated. Purification by column chromatography on silica gel (100% ethylacetate in hexane) followed by washing with hexane and ether afforded 22 mg of the product (41.15% yield).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. custompartitioned between ethylacetate and water
  3. washThe organic layer was washed with water, brine solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (100% ethylacetate in hexane)
  7. washby washing with hexane and ether

Sources & evidence

ORD record
ord-40797fdd06d142dfa17977c7cb02ddaa
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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