Triphenylphosphine → 2-((4-Fluorotetrahydro-2h-pyran-4-yl)methoxy)-5-iodo-3-(trifluoromethyl)pyridine

HRID 574857Notes

Reaction equation

HRID 574857 reaction equation
[F:1][C:2]1([CH2:8][OH:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[I:10][C:11]1[CH:12]=[C:13]([C:18]([F:21])([F:20])[F:19])[C:14](O)=[N:15][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)(C)C)=O)=N\C(OC(C)(C)C)=O>O1CCCC1>[F:1][C:2]1([CH2:8][O:9][C:14]2[C:13]([C:18]([F:19])([F:21])[F:20])=[CH:12][C:11]([I:10])=[CH:16][N:15]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 56971676(4-Fluorooxan-4-yl)methanolHCID 178517797HCID 178517797, compound

Product 1

HCID 671266522-((4-Fluorotetrahydro-2h-pyran-4-yl)methoxy)-5-iodo-3-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of EXAMPLE 37C (0.537 g), 5-iodo-3-(trifluoromethyl)pyridin-2-ol (1.156 g), and triphenylphosphine (1.574 g) in tetrahydrofuran (20 mL) was cooled to 0° C. To this solution was added (E)-di-tert-butyl diazene-1,2-dicarboxylate (0.921 g). The reaction mixture was stirred overnight. The solvent was removed, and the residue was purified with column flash chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate to give the desired product.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified with column flash chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b34ead4c6b2e4e4fa5c2d756e5cbf437
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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