Dimethylformamide → HCID 21947595, compound

HRID 2214431Notes

Reaction equation

HRID 2214431 reaction equation
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH:3]=[CH2:4].B1[CH:21]2[CH2:22]CC[CH:17]1[CH2:18][CH2:19][CH2:20]2.C(=O)([O-])[O-].[K+].[K+].C[N:32](C=O)C>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2].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.[Fe+2]>[CH3:22][C:21]1[N:32]=[CH:17][C:18]([CH2:4][CH2:3][CH2:2][CH2:1][N:5]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:15])=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 339432N-(3-Buten-1-yl)phthalimide2×

Product 1

HCID 21947595HCID 21947595, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 2-3 (12.7 g, 63.2 mmol) was added a solution of 9-BBN in THF (132 mL of a 0.5 M solution, 65.8 mmol). After stirring for 15 hours, potassium carbonate powder (14.5 g, 105 mmol) and 2-3 (12.7 g, 52.7 mmol) was added. To this mixture was then added a premixed, degassed, aged (80° C. for 30 minutes with vigorous stirring) suspension of Pd(OAc)2 (1.78 g, 7.9 mmol) and DPPF (4.96 g, 8.9 mmol) in DMF (50 mL) via a cannula, and the resulting mixture degassed with argon bubbling for 30 minutes. The mixture was then heated at 70° C. for 3 hours. Following cooling, the mixture was reduced to a thick slurry, diluted with ether, washed with water and brine. The organics were dried over MgSO4 and concentrated to give a brown oil. This residue was chromatographed on silica gel (40–60% EtOAc/hexanes) to give 2-4 (9.6 g) as a yellow solid.

Workup

  1. additionTo this mixture was then added a premixed
  2. customdegassed
  3. customthe resulting mixture degassed with argon bubbling for 30 minutes
  4. temperatureFollowing cooling
  5. additiondiluted with ether
  6. washwashed with water and brine
  7. dry with materialThe organics were dried over MgSO4
  8. concentrationconcentrated
  9. customto give a brown oil
  10. customThis residue was chromatographed on silica gel (40–60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a3f5605e237b4ca68423c0c568881fbb
Source dataset
uspto-grants-2006_09
Patent number
US07109191B2

Reaction notes

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