Triphenylphosphine → HCID 21110948, compound

HRID 425905Notes

Reaction equation

HRID 425905 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([OH:14])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[O:15][CH:16]([C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=1[Cl:26])[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:46]1([CH2:52][CH2:53]O)[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1.CCOC(/N=N/C(OCC)=O)=O>>[Cl:26][C:19]1[C:20]([F:25])=[CH:21][CH:22]=[C:23]([Cl:24])[C:18]=1[CH:16]([O:15][C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH2:53][CH2:52][N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)=[CH:12][CH:13]=2)[CH:6]=[N:7][C:2]=1[NH2:1])[CH3:17]

Participants

5

Reactant 4

HCID 11776Triphenylphosphine3×HCID 611632-MorpholinoethanolHCID 5462977Diethyl azodicarboxylate3×HCID 178466005HCID 178466005, compound

Product 1

HCID 21110948HCID 21110948, compoundYield 53%

Procedure

To a mixture of 6′-amino-5′-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-[3,3′]bipyridinyl-6-ol (78 mg, 0.20 mmol), triphenyphosphine (63 mg, 0.24 mmol) and 2-morpholin-4-yl-ethanol (0.026 mL, 0.22 mmol) was added DEAD (0.034 mL, 0.22 mmol). After stirring overnight more PPh3 (63 mg, 0.24 mmol) and more DEAD (0.034 mL, 0.22 mmol) were added. After several hours, more alcohol (0.026 mL, 0.22 mmol) was added. After several more hours, more PPh3 (63 mg, 0.24 mmol) and more DEAD (0.034 mL, 0.22 mmol) were added. After stirring overnight, the mixture was partitioned between dichloromethane and half-saturated brine. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, methanol to afford 5-[1-(2,6-Dichloro-3-fluoro-phenyl)-ethoxy]-6′-(2-morpholin-4-yl-ethoxy)-[3,3′]bipyridinyl-6-ylamine (53 mg, 53%).

Workup

  1. additionwere added
  2. waitAfter several hours
  3. waitAfter several more hours
  4. customthe mixture was partitioned between dichloromethane and half-saturated brine
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with dichloromethane
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by silica gel chromatography
  10. washelution of dichloromethane, methanol

Sources & evidence

ORD record
ord-2e9516673d4f46c1a4053e5d12ec643b
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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