Triphenylarsine → HCID 67378027, compound

HRID 710582Notes

Reaction equation

HRID 710582 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[C:7](=[O:20])[N:8]([CH3:19])[C:9]2[C:14]([CH:15]=1)=[CH:13][N:12]=[C:11]([NH:16][CH2:17][CH3:18])[CH:10]=2)CCC.[C:29]([N:36]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:37]1[C:42]([F:43])=[C:41](I)[C:40]([F:45])=[CH:39][N:38]=1)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].[As](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cu]I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:32]([O:31][C:29]([N:36]([C:37]1[C:42]([F:43])=[C:41]([C:6]2[C:7](=[O:20])[N:8]([CH3:19])[C:9]3[C:14]([CH:15]=2)=[CH:13][N:12]=[C:11]([NH:16][CH2:17][CH3:18])[CH:10]=3)[C:40]([F:45])=[CH:39][N:38]=1)[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[O:30])([CH3:33])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 11773TriphenylarsineHCID 67366299HCID 67366299, compoundHCID 67378363HCID 67378363, compound

Product 1

HCID 67378027HCID 67378027, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
60 °C

Procedure

A tube was charged 3-(tributylstannyl)-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one (48 mg, 0.1 mmol), N,N-bis-BOC-3,5-difluoro-4-iodopyridin-2-amine (54 mg, 0.12 mmol), Ph3As (25 mg, 0.08 mmol), CuI (7.5 mg, 0.04 mmol) and Pd2(dba)3 (9 mg, 0.01 mmol). The tube was degassed and refilled with nitrogen gas. DMF (10 mL) was added, and then the tube was sealed and heated at 60° C. for 48 h. Aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel (70% ethyl acetate in hexanes eluant) to provide the title compound. MS (m/z) 533.2 (M+1).

Workup

  1. customThe tube was degassed
  2. additionrefilled with nitrogen gas
  3. additionDMF (10 mL) was added
  4. customthe tube was sealed
  5. additionAqueous sodium bicarbonate solution was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe combined organic layers were washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was chromatographed on silica gel (70% ethyl acetate in hexanes eluant)

Sources & evidence

ORD record
ord-dcf75afb07bd454090facc841b439dc7
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Reaction notes

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