Sodium Carbonate → HCID 68773882, compound

HRID 1970954Notes

Reaction equation

HRID 1970954 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10](=O)[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[N:6][CH:7]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([NH2:24])=[NH:23].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:24]=[C:22]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=3)[N:23]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 556504PicolinimidamideHCID 687701071-(5-Bromo-pyridin-3-yl)-4,4-dimethyl-pent-1-yn-3-one

Product 1

HCID 68773882HCID 68773882, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-bromo-pyridin-3-yl)-4,4-dimethyl-pent-1-yn-3-one (1 eq, 770 mg, 2.89 mmol) in THF (12 ml) is added pyridine-2-carboxamidine (1.5 eq, 684 mg, 4.34 mmol) and Na2CO3 (2.4 eq, 736 mg, 6.94 mmol). The resulting mixture is heated using microwave radiation for 1 h at 150° C. The solvent is removed in vacuo and the residue is partitioned between sat. aqueous NaHCO3 solution and DCM. The organic portion is dried (MgSO4) and concentrated in vacuo. The resulting residue is purified using column chromatography (DCM/MeOH) to give the title compound; [M+H]+=369/371.

Workup

  1. temperatureThe resulting mixture is heated
  2. customfor 1 h
  3. customat 150° C
  4. customThe solvent is removed in vacuo
  5. customthe residue is partitioned between sat. aqueous NaHCO3 solution and DCM
  6. dry with materialThe organic portion is dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue is purified

Sources & evidence

ORD record
ord-ad4a642187574e2980cfbbcda44f50f6
Source dataset
uspto-grants-2013_04
Patent number
US08431578B2

Reaction notes

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