3-Bromopyridine → HCID 66801964, compound

HRID 1843835Notes

Reaction equation

HRID 1843835 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][C:5](=[O:10])[C:4]=2[CH:3]=[CH:2]1.Br[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([N:6]2[CH2:7][CH2:8][C:9]3[S:1][CH:2]=[CH:3][C:4]=3[C:5]2=[O:10])[CH:13]=1

Participants

6

Reactant 3

HCID 122863-BromopyridineHCID 62657Potassium Phosphate, TribasicHCID 203468586.7-dihydrothieno[3.2.c]pyridin-4(5H)-one

Product 1

HCID 66801964HCID 66801964, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one (I-7d: 80 mg, 0.5221 mmol) was reacted with 3-bromo-pyridine (99 mg, 0.6266 mmol), 1,4-dioxane (15 mL), copper iodide (9.9 mg, 0.05221 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (22.2 mg, 0.15667 mmol) and potassium phosphate (277.1 mg, 1.3054 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in DCM) afforded 60 mg of the product (50% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1% methanol in DCM)

Sources & evidence

ORD record
ord-39b8c48225a34cc29e19d14538c575c0
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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