Triphenylphosphine → tert-butyl {(1S)-2-[(6-chloro-5-fluoropyridin-3-yl)oxy]-1-methylethyl}carbamate

HRID 1026218Notes

Reaction equation

HRID 1026218 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].O[CH2:11][C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13].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>C1(C)C=CC=CC=1.C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:13][C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH3:11])=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamateHCID 404247372-Chloro-3-fluoro-5-hydroxypyridine

Product 1

HCID 86666267tert-butyl {(1S)-2-[(6-chloro-5-fluoropyridin-3-yl)oxy]-1-methylethyl}carbamateYield 57.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-chloro-5-fluoropyridin-3-ol (2.43 g), tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (3.46 g), triphenylphosphine (6.48 g) and THF (25 mL) was added dropwise a toluene solution (1.9 M, 13.0 mL) of diisopropyl azodicarboxylate at room temperature, and the obtained mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.88 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-120748e3ad644b7bade63cbfe832074b
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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