Potassium Phosphate, Tribasic → HCID 66807275, compound

HRID 1843987Notes

Reaction equation

HRID 1843987 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]3[CH2:20][CH2:21][NH:22][C:23](=[O:24])[C:5]=3[C:4]=2[CH:3]=1.I[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[CH3:32].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([S:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)(=[O:13])=[O:12])[C:6]3[CH2:20][CH2:21][N:22]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][C:31]=4[CH3:32])[C:23](=[O:24])[C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 66803517HCID 66803517, compound

Product 1

HCID 66807275HCID 66807275, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions and work up as described for the preparation of Example 1A, 8-fluoro-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (I-60a: 450 mg, 1.308 mmol) was reacted with 3-iodo-4-methylpyridine (286 mg, 1.308 mmol), 1,4-dioxane (25 mL), copper iodide (25 mg, 0.13 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (58.46 mg, 0.392 mmol) and potassium phosphate (693 mg, 3.27 mmol) at 120° C. overnight to afford the crude product. Purification by column chromatography on silica gel (5% methanol in DCM) afforded 60 mg of the product (15% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (5% methanol in DCM)

Sources & evidence

ORD record
ord-10476a97d6eb4bb38f65d7970561890a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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