Triphenylphosphine → HCID 67981122, compound

HRID 1520005Notes

Reaction equation

HRID 1520005 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.O[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.[N+:24]([C:27]1[CH:28]=[N:29][NH:30][CH:31]=1)([O-:26])=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N+:24]([C:27]1[CH:28]=[N:29][N:30]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH:31]=1)([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 729214-PyridineethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 67981122HCID 67981122, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

DIAD (7.27 mL; 37.2 mmol; 1.1 eq.) was added slowly into a solution of 4-(2-hydroxyethyl)pyridine (4.2 g; 34.1 mmol; 1.0 eq.), 4-nitro-1H-pyrazole (3.86 g; 34.1 mmol; 1.0 eq.) and triphenylphosphine (9.84 g; 37.5 mmol; 1.1 eq.) in THF (120 mL) maintained under nitrogen at 0° C. The reaction mixture was allowed to warm to RT and left O/N. THF was removed under reduced pressure and the crude was purified by flash chromatography on silica (EtOAc:heptane, gradient from 50:50 to 100:0) to afford the title compound in quantitative yield. MS (ESI+): 219.0, (ESI−) 272.1 (purity 92.2%). 1H NMR (400 Mz, DMSO-d6) δ 8.80 (s, 1H), 8.44-8.43 (m, 2H), 8.24 (s, 1H), 7.18-7.17 (m, 2H), 4.50-4.48 (t, J=7.04 Hz, 2H), 3.19-3.17 (t, J=7.0 Hz, 2H).

Workup

  1. temperatureto warm to RT
  2. waitleft O/N
  3. customTHF was removed under reduced pressure
  4. customthe crude was purified by flash chromatography on silica (EtOAc:heptane, gradient from 50:50 to 100:0)

Sources & evidence

ORD record
ord-5b5a7486a51541f69c4db2fe1f7342b6
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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