Triphenylphosphine → 3-fluoro-N-{2-[2-(trimethylsilyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]ethyl}benzamide

HRID 2425502Notes

Reaction equation

HRID 2425502 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[F:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([NH:15][CH2:16][CH2:17][C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(=O)C.[Na+].[Cl-].[Li+]>CN(C)C=O.C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[F:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([NH:15][CH2:16][CH2:17][C:18]1[C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[NH:8][C:19]=1[Si:20]([CH3:22])([CH3:21])[CH3:23])=[O:14]

Participants

10

Reactant 5

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 517045Sodium AcetateHCID 15165104-Amino-3-iodopyridineHCID 672549453-fluoro-N-[4-(trimethylsilyl)-3-butynyl]benzamide

Product 1

HCID 672549103-fluoro-N-{2-[2-(trimethylsilyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]ethyl}benzamide

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 3-iodo-4-pyridineamine (594 mg), 3-fluoro-N-[4-(trimethylsilyl)-3-butynyl]benzamide (710 mg), palladium acetate (61 mg), triphenylphosphine (142 mg), sodium acetate (443 mg) and lithium chloride (115 mg) in N,N-dimethylformamide (6 mL) and acetonitrile (3 mL) was irradiated with microwave (100 W) for 30 minutes, poured into water and then extracted with ethyl acetate. The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (parallel separation purification system) to obtain the titled compound having the following physical properties (404.8 mg).

Workup

  1. customwas irradiated with microwave (100 W) for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (parallel separation purification system)

Sources & evidence

ORD record
ord-91dab7bc135541e79dc0622d8825e9d1
Source dataset
uspto-grants-2011_06
Patent number
US07964726B2

Reaction notes

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