4-Hydroxymethylpyridine → HCID 67235215, compound

HRID 1748317Notes

Reaction equation

HRID 1748317 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[N:9]1[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:15][C:12]2[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 97268Di-tert-butyl azodicarboxylate

Product 1

HCID 67235215HCID 67235215, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-nitro-1H-pyrazole (211 mg, 1.87 mmol), pyridine-4-methanol (0.28 mL, 2.56 mmol), and triphenylphosphine (538 mg, 2.05 mmol) in THF (10 mL) under nitrogen is added di-t-butyl azodicarboxylate (472 mg, 2.05 mmol) over 3 min. The reaction mixture was stirred for 16 h at room temperature. The mixture is concentrated and is purified by flash column chromatography using a gradient of 0-3% methanol in CH2Cl2 to afford the title compound as a yellow oil (247 mg, 65%).

Workup

  1. concentrationThe mixture is concentrated
  2. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-c73b967e1b5c420e85137c5d395e400b
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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