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Triphenylphosphine → HCID 59678685, compound

HRID 1479253
Notes
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Reaction equation

HRID 1479253 reaction equation
[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][CH:9]([OH:11])[CH3:10])=[CH:5][CH:4]=1.[C:14]([N:18]1[C:23](=[O:24])[C:22]([Cl:25])=[C:21](O)[CH:20]=[N:19]1)([CH3:17])([CH3:16])[CH3:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O>[C:14]([N:18]1[C:23](=[O:24])[C:22]([Cl:25])=[C:21]([O:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH:9]([OH:11])[CH3:10])=[CH:12][CH:13]=2)[CH:20]=[N:19]1)([CH3:17])([CH3:15])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 17755959HCID 17755959, compoundHCID 546869462-tert-Butyl-4-chloro-5-hydroxypyridazin-3(2H)-one

Product 1

HCID 59678685HCID 59678685, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

To solution of the product of Example 6B (269 mg, 1.48 mmol) and 2-tert-butyl-4-chloro-5-hydroxy-2H-pyridazin-3-one (250 mg, 1.23 mmol) dissolved in anhydrous THF (18.5 mL) was added solid PPh3 (485 mg, 1.85 mmol) and DIAD (0.358 mL, 1.85 mmol). After completion of addition the reaction mixture continued to stir at room temperature. After 20 hours, the reaction mixture was diluted with water. The aqueous layer was separated and extracted with ethyl acetate (3×). All combined organic layers were dried over Na2SO4, filtered, and concentrated to provide an oil. The crude material was purified using silica gel chromatography (1:1 pentane:ethyl acetate) to provide the desired product (234 mg, 0.634 mmol) in 51% yield. 1H (CDCl3 7.71 (1H, s), 7.33 (2H, d, 600 MHz): δ J=8.7 Hz), 6.94 (2H, d, J=8.7 Hz), 5.24 (2H, s), 4.19 (1H, m), 3.95 (1H, dd, J=9.2, 3.1 Hz), 3.81 (1H, dd, J=9.2, 7.7 Hz), 1.62 (9H, s) 1.29 (3H, d, J=6.4 Hz).

Workup

  1. additionAfter completion of addition the reaction mixture
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialAll combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide an oil
  8. customThe crude material was purified

Sources & evidence

ORD record
ord-04fd024eb1fc477787b6502f2633b014
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09408927B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes