Sodium Carbonate → HCID 86699395, compound

HRID 1777562Notes

Reaction equation

HRID 1777562 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1I.[F:12][C:13]1[CH:14]=[C:15]([CH:37]=[CH:38][CH:39]=1)[CH2:16][C:17]1[CH:36]=[CH:35][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]#[C:27][Si:28]([CH2:33][CH3:34])([CH2:31][CH3:32])[CH2:29][CH3:30])=[O:22])=[CH:19][CH:18]=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:8]([C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:27]([Si:28]([CH2:33][CH3:34])([CH2:31][CH3:32])[CH2:29][CH3:30])=[C:26]2[CH2:25][CH2:24][NH:23][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C:15]2[CH:37]=[CH:38][CH:39]=[C:13]([F:12])[CH:14]=2)=[CH:36][CH:35]=1)(=[O:10])[CH3:9]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 11032652Ethanone, 1-(4-amino-3-iodophenyl)-HCID 67974550HCID 67974550, compound

Product 1

HCID 86699395HCID 86699395, compoundYield 21.3%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

1-(4-Amino-3-iodophenyl)ethanone (0.100 g; 0.383 mmol), 4-(3-fluorobenzyl)-N-(4-(triethylsilyl)but-3-ynyl)benzamide 0.151 g; 0.383 mmol), bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.016 g; 0.019 mmol), lithium chloride (0.016 mg; 0.383 mmol) and sodium carbonate (0.081 g; 0.766 mmol) were suspended in DMF (5 mL) and the mixture was stirred at 100° C. for 18 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 0.043 g (21%) of the title compound as a yellow oil.

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-afd489a16d024612a7a0b7ae0a75db70
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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