Sodium Carbonate → HCID 86699394, compound

HRID 1777560Notes

Reaction equation

HRID 1777560 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1I.[F:11][C:12]1[CH:13]=[C:14]([CH:36]=[CH:37][CH:38]=1)[CH2:15][C:16]1[CH:35]=[CH:34][C:19]([C:20]([NH:22][CH2:23][CH2:24][C:25]#[C:26][Si:27]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:28][CH3:29])=[O:21])=[CH:18][CH:17]=1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[C:6]([C:5]1[CH:4]=[C:3]2[C:2](=[CH:9][CH:8]=1)[NH:1][C:26]([Si:27]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:28][CH3:29])=[C:25]2[CH2:24][CH2:23][NH:22][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C:14]2[CH:36]=[CH:37][CH:38]=[C:12]([F:11])[CH:13]=2)=[CH:35][CH:34]=1)#[N:7]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 44163954-Amino-3-iodobenzonitrileHCID 67974550HCID 67974550, compound

Product 1

HCID 86699394HCID 86699394, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Amino-3-iodobenzonitrile (0.10 g; 0.41 mmol), 4-(3-fluorobenzyl)-N-(4-(triethylsilyl)but-3-ynyl)benzamide (0.162 g; 0.41 mmol) bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.017 g; 0.020 mmol), lithium chloride (0.017 mg; 0.410 mmol) and sodium carbonate (0.087 g; 0.820 mmol) were suspended in DMF (5 mL) and the mixture was stirred at 100° C. for 15 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane) to afford 0.056 g (27%) of the title compound as a white solid.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additiondiluted in ethyl acetate
  3. washThe organic layer was successively washed with brine, sodium thiosulfate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-2ed352248dc64184bedba9303ef88829
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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