Sodium Carbonate → HCID 178418705, compound

HRID 1060055Notes

Reaction equation

HRID 1060055 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C([O-])(=O)C.[K+].C([O:23][N:24]=[C:25]1[C:33]2([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:32]2[C:27](=[CH:28][CH:29]=[C:30](Br)[CH:31]=2)[NH:26]1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.Cl[Pd]Cl>[OH:23][N:24]=[C:25]1[C:33]2([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:4]3[CH:5]=[C:6]([CH:7]=[C:2]([F:1])[CH:3]=3)[C:8]#[N:9])[CH:31]=2)[NH:26]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 27833303-Bromo-5-fluorobenzonitrileHCID 178419047HCID 178419047, compound

Product 1

HCID 178418705HCID 178418705, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-fluoro-5-cyano-bromobenzene (0.4 g, 2.0 mmol) in dry DMF (10 ml) was added diboron pinacolate ester (0.63 g, 2.5 mmol), potassium acetate (0.65 g, 6.7 mmol) and PdCl2 (dppf) (0.2. g) and the reaction was heated to 80° C. under a nitrogen atmosphere. After 8 h. from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (0.2 g, 0.5 mmol), PdCl2 (dppf) (0.05 g) and sodium carbonate (1.30 g, 12.5 mmol) were added and heating at 80° C. was continued. After 8 h. the reaction was cooled and partitioned between water and ethyl acetate, the organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20) to give the desired product (0.14 g, 0.33 mmol, 66%).

Workup

  1. temperatureheating at 80° C.
  2. temperatureAfter 8 h. the reaction was cooled
  3. custompartitioned between water and ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20)

Sources & evidence

ORD record
ord-b0a092ea124f45759969152c41e248e7
Source dataset
uspto-grants-2003_02
Patent number
US06521657B2

Reaction notes

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