Nitroethane → HCID 23502824, compound

HRID 1835350Notes

Reaction equation

HRID 1835350 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][N:7]([CH3:25])[C:8](=[O:24])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:22]#[CH:23])=[N:11][CH:10]=1.[N+:35]([CH2:38][CH3:39])([O-])=[O:36].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(#N)C.C1(C)C=CC=CC=1>[F:30][C:29]([F:32])([F:31])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([C:2]([F:33])([F:1])[F:34])[CH:28]=1)[CH2:6][N:7]([CH3:25])[C:8](=[O:24])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:22]2[O:36][N:35]=[C:38]([CH3:39])[CH:23]=2)=[N:11][CH:10]=1

Participants

6

Reactant 3

HCID 6587Nitroethane2×HCID 90495Di-tert-butyl dicarbonate2×HCID 23502779N-(3,5-Bis-trifluoromethyl-benzyl)-6-ethynyl-N-methyl-4-o-tolyl-nicotinamide

Product 1

HCID 23502824HCID 23502824, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 55 mg (0.12 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-ethynyl-N-methyl-4-o-tolyl-nicotinamide (Example 63), 0.026 ml (0.35 mmol) nitroethane and 1 mg (0.01 mmol) 4-N,N-dimethylaminopyridine in 0.5 ml acetonitrile a solution of 77 mg (0.35 mmol) di-tert-butyl dicarbonate in 0.1 ml toluene was added, and the mixture was stirred at room temperature over night. Another portion of 0.026 ml (0.35 mmol) nitroethane and 77 mg (0.35 mmol) di-tert-butyl dicarbonate were added, and stirring was continued for 24 h. Quenching with water was followed by extraction with two portions of ethyl acetate. The combined organic extracts were dried with sodium sulfate and concentrated. Column chromatography afforded 21 mg (34%) of the title compound as a light yellow amorphous mass.

Workup

  1. stirringstirring
  2. customQuenching with water
  3. extractionwas followed by extraction with two portions of ethyl acetate
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f00fa032a619439cbaa34af33e339333
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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