Dimethylformamide → HCID 58431082, compound

HRID 1040439Notes

Reaction equation

HRID 1040439 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[N:26]=[C:25]([N:27]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH:24]=[CH:23][CH:22]=1.[CH3:46][N:47](C=O)C>CC([O-])=O.CC([O-])=O.[Pd+2].[C-]#N.[C-]#N.[Zn+2]>[CH3:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][N:27]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:25]2[N:26]=[C:21]([C:46]#[N:47])[CH:22]=[CH:23][CH:24]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 6228Dimethylformamide2×HCID 11776TriphenylphosphineHCID 58431001HCID 58431001, compound

Product 1

HCID 58431082HCID 58431082, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 167845palladium(II) acetateCatalyst

Procedure

Polystyrene supported triphenylphosphine (250 mg, 0.544 mmol) and Pd(OAc)2 (57 mg, 0.25 mmol) were combined in a glass vial along with DMF (5.5 mL). The vial was flushed with argon and a septum was affixed. The suspension was stirred for 1 h at room temperature. Solid Zn(CN)2 (426 mg, 3.63 mmol) and a solution of (6-bromo-pyridin-2-yl)-bis-(4-methoxy-benzyl)-amine (1.50 g, 3.63 mmol) in DMF (5.5 mL) were then added. The vial was flushed with argon, sealed, and heated at 140° C. in a microwave for 30 min. The reaction mixture was filtered and the volatiles were removed in vacuo. The residue was purified by flash chromatography on silica gel (10→50% EtOAc/hexanes) to give the title compound as a colorless oil, m/z 361.0 [M+2]+.

Workup

  1. customThe vial was flushed with argon
  2. customThe vial was flushed with argon
  3. customsealed
  4. temperatureheated at 140° C. in a microwave for 30 min
  5. filtrationThe reaction mixture was filtered
  6. customthe volatiles were removed in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (10→50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c028b2092b494106a78b4fa38b9234a0
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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