Triphenylphosphine → HCID 68530630, compound

HRID 644282Notes

Reaction equation

HRID 644282 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:28])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[OH:26])=[N:6][CH:7]=1.O[CH:30]1[CH2:39][CH2:38][C:33]2([O:37][CH2:36][CH2:35][O:34]2)[CH2:32][CH2:31]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CN(C=O)C.CCOCC.C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:28])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[O:26][CH:30]2[CH2:39][CH2:38][C:33]3([O:37][CH2:36][CH2:35][O:34]3)[CH2:32][CH2:31]2)=[N:6][CH:7]=1

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5673521,4-Dioxaspiro(4.5)decan-8-olHCID 21075346HCID 21075346, compound

Product 1

HCID 68530630HCID 68530630, compoundYield 70.3%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(5-Chloropyridin-2-yl)-5-fluoro-2-(4-fluoro-2-hydroxybenzoylamino)-benzamide (1.62 g, 4 mmol), 8-hydroxy-1,4-dioxa-spiro[4.5]decane (630 mg, 4 mmol), and triphenylphosphine (1.04 g, 4 mmol) were dissolved in 4 mL dry DMF, 2 mL dry methylene chloride, and 6 mL dry THF. The resulting slurry was sonicated for 5 min, and then diisopropyl azodicarboxylate (DIAD, 0.8 mL, 4 mmol) was added; and the mixture was sonicated for 2 h. Ether (40 mL) was added, and the mixture was cooled in the freezer overnight. Triphenylphosphine oxide was filtered off, and the resulting solution was concentrated to dryness under reduced pressure. Flash chromatography on silica gel gave the crude product (1.53 g) as a viscous, colorless oil which was used without further purification.

Workup

  1. customThe resulting slurry was sonicated for 5 min
  2. customand the mixture was sonicated for 2 h
  3. temperaturethe mixture was cooled in the freezer overnight
  4. filtrationTriphenylphosphine oxide was filtered off
  5. concentrationthe resulting solution was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e784b19cef2e4d149b2786056f831e34
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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