Potassium Phosphate, Tribasic → HCID 89964208, compound

HRID 1843902Notes

Reaction equation

HRID 1843902 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[CH2:5][CH2:4][NH:3]1.I[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[CH3:21].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:21][C:20]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[N:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][C:9]([C:12]#[N:13])=[CH:8][CH:7]=2)[C:2]1=[O:1]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 680941261-Oxo-1,2,3,4-tetrahydroisoquinoline-7-carbonitrile

Product 1

HCID 89964208HCID 89964208, compoundYield 38.14%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 1-oxo-1,2,3,4-tetrahydro-isoquinoline-7-carbonitrile (I-32c: 120 mg, 0.6976 mmol) was reacted with 3-iodo-4-methyl-pyridine (152.7 mg, 0.6976 mmol), 1,4-dioxane (5 mL), copper iodide (13.2 mg, 0.06976 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (40 mL, 0.2092 mmol) and potassium phosphate (369.7 mg, 1.744 mmol) to afford the crude product. Purification by column chromatography on silica gel (80% ethylacetate in hexane) afforded 70 mg of the product (38.14% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (80% ethylacetate in hexane)

Sources & evidence

ORD record
ord-49fcaafc17754a9d947b7f2c6cacd1e2
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…