Triethylamine → HCID 178476771, compound

HRID 574657Notes

Reaction equation

HRID 574657 reaction equation
[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:29])=[N:19][C:20]([N:23]2[CH:27]=[C:26](I)[CH:25]=[N:24]2)=[N:21][CH:22]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][PH:31]([O-])([O-:35])[O:32][CH2:33][CH3:34].CCN(CC)CC>CN(C=O)C.O.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]>[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:29])=[N:19][C:20]([N:23]2[CH:27]=[C:26]([P:31]([CH3:30])(=[O:35])[O:32][CH2:33][CH3:34])[CH:25]=[N:24]2)=[N:21][CH:22]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 178476778HCID 178476778, compoundHCID 178522802HCID 178522802, compound2×

Product 1

HCID 178476771HCID 178476771, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of product of step C, compound 1-1-c, (1.2 g, 2.4 mmol), ethyl methyl-phosphite (522 mg, 4.8 mmol) and Et3N (610 mg, 6 mmol) in DMF (20 mL) was added PdCl2(dppf) (176 mg). The mixture was allowed to stir overnight at 80° C. The mixture was cooled to room temperature and diluted with water. The resulting mixture was then filtered and the filtrate was extracted with dichloromethane/methanol (5/1). The organic layer was dried over sodium sulfate and concentrated under vacuum. And the residue was purified over silica gel (dichloromethane:methanol=3/1) to provide the product, 1-1-d, (500 mg, 44%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe resulting mixture was then filtered
  3. extractionthe filtrate was extracted with dichloromethane/methanol (5/1)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customAnd the residue was purified over silica gel (dichloromethane:methanol=3/1)
  7. customto provide the product, 1-1-d, (500 mg, 44%)

Sources & evidence

ORD record
ord-0aa13b13be5c4cee93ee209ce49e772e
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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