Potassium Phosphate, Tribasic → HCID 66807276, compound

HRID 1843992Notes

Reaction equation

HRID 1843992 reaction equation
[C:1]1(=[O:14])[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.I[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[CH3:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:22][C:21]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N:2]1[CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:1]1=[O:14]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 873712,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indol-1-oneHCID 144235133-Iodo-4-methylpyridine

Product 1

HCID 66807276HCID 66807276, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (I-61e: 250 mg, 1.34 mmol) was reacted with 3-iodo-4-methylpyridine (294.3 mg, 1.34 mmol), 1,4-dioxane (10 mL), copper iodide (25.6 mg, 0.134 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (59.8 mg, 0.402 mmol) and potassium phosphate (710 mg, 3.35 mmol) at 120° C. overnight to afford the crude product. Purification by column chromatography on silica gel (40% ethyl acetate in hexane), followed by preparative HPLC afforded 5 mg of the product (2% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-cf4bf7d5743e4e438a01b2aa0f12300e
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…