Dimethylformamide → HCID 11683167, compound

HRID 2427536Notes

Reaction equation

HRID 2427536 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[CH2:5]2.[C:20](=[O:23])([O-])[O-:21].[K+].[K+].[CH3:26][N:27]([CH:29]=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:4]([O:21][C:20]([N:27]1[CH2:29][CH:2]=[C:10]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH2:5]3)[CH2:9][CH2:26]1)=[O:23])([CH3:8])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 57949631HCID 57949631, compound

Product 1

HCID 11683167HCID 11683167, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

5-Bromo-2-(4-methyl-benzyl)-2,3-dihydro-isoindol-1-one (25 mg, 0.080 mmol), 4-boranate ester-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (24 mg, 0.079 mmol), potassium carbonate (32 mg, 0.24 mmol), PdCl2(dppf) (3.8 mg, 0.005 mmol), was stirred in DMF (3 mL) at 110° C. for 18 hours, under argon. The cooled reaction was concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Column chromatography (40% EtOAc/Hexanes) provided the title compound as a yellow solid (8.1 mg, 25%). 1H NMR (300 MHz, CDCl3): δ 7.85 (d, 1H), 7.49 (d, 1H), 7.36 (s, 1H), 7.20 (q, 4H), 6.11 (br s, 1H), 4.78 (s, 2H), 4.26 (s, 2H), 4.10 (dd, 2H, 3.66 (t, 2H, 2.53 (br s, 2H), 2.35 (s, 3H), 1.51 (s, 9H).

Workup

  1. customThe cooled reaction
  2. concentrationwas concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3e2b56c9531d4b0bba7018818675fe16
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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