Triphenylphosphine → HCID 21934103, compound

HRID 891386Notes

Reaction equation

HRID 891386 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([OH:16])=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:46][C:47]([F:54])([F:53])[CH:48]([CH3:52])[CH2:49][CH2:50]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C:13]([O:16][CH2:50][CH2:49][CH:48]([C:47]([F:54])([F:53])[F:46])[CH3:52])=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2743554,4,4-Trifluoro-3-methyl-1-butanolHCID 5363146Diisopropyl azodicarboxylateHCID 178504688HCID 178504688, compound

Product 1

HCID 21934103HCID 21934103, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(3,4-difluorophenyl)-4-hydroxy-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone (189 mg, 0.5 mmol), Ph3P (262 mg, 1 mmol) and 3-trifluoromethyl-1-butanol (66 mg, 0.5 mmol) in THF (25 mL) was added dropwise a solution of DIAD (0.2 mL, 1 mmol) in THF (5 mL) and the resulting mixture was stirred at room temperature for 8 hours. The mixture was concentrated in vacuo and the residue was chromatographed (silica gel, 1:1 hexanes-ethyl acetate) to provide the desired product, (yield: 180 mg 71%). mp 126-128° C. 1H NMR (300 MHz, DMSO-d6) δ 0.96 (d, J=7 Hz, 3H), 1.55 (m, 1H), 1.97 (m, 1H), 2.30 (m, 1H), 3.29 (s, 3H), 4.46 (m, 2H), 7.52 (m, 1H), 7.62 (m, 1H), 7.81 (m, 1H), 7.90 (d, J=9 Hz, 2H), 8.08 (d, J=9 Hz, 2H), 8.22 (s, 1H). MS (APCI+) m/z 503 (M+H)+; (APCI−) m/z 537 (M+Cl)−. Anal. calc. for C22H19F5N2O4S: C, 52.59; H, 3.81; N, 5.57. Found: C, 52.70; H, 3.73; N, 5.63.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was chromatographed (silica gel, 1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-5002f2bad4da43b09ca3fa8e787e1fbe
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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