Triphenylphosphine → HCID 21110948, compound

HRID 2266683Notes

Reaction equation

HRID 2266683 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), triphenylphosphine (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-053b0b7ca2634a72becb2f9ac250064b
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

Loading…