Dimethylformamide → HCID 2797997, compound

HRID 929438Notes

Reaction equation

HRID 929438 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].CN(C=O)C>>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)=[CH:19][CH:20]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 73934-tert-ButylphenolHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 2797997HCID 2797997, compoundYield 95.3%

Procedure

Following procedure A, 2-chloro-5-nitropyridine (501 mg, 3.16 mmol, 1.00 eq) and 4-tert-butylphenol (611 mg, 4.07 mmol, 1.29 eq) were dissolved in DMF (6.0 mL) Anhydrous K2CO3 (654 mg, 4.73 mmol, 1.50 eq) was added and the reaction mixture was stirred at room temperature for 14 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100 to 1:50) to afford the title compound as colourless solid (820 mg, 3.01 mmol, 95% yield). Rf=0.40 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C15H17N2O3+[M+H]+ 273.1234. found: 273.1229. 1H NMR (400 MHz, CDCl3) δ 9.06 (d, J=2.8 Hz, 1H, aromatic H), 8.46 (dd, J=9.1, 2.8 Hz, 1H, aromatic H), 7.53-7.42 (m, 2H, aromatic H), 7.17-7.05 (m, 2H, aromatic H), 7.01 (d, J=9.1 Hz, 1H, aromatic H), 1.35 (s, 9H, C(CH3)3). 13C NMR (101 MHz, CDCl3) δ 167.20, 150.49, 148.98, 145.26, 140.29, 134.95, 126.99, 120.84, 111.38, 34.72, 31.57.

Workup

  1. additionwas added
  2. extractionAfter extraction with Et2O
  3. customthe crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100 to 1:50)

Sources & evidence

ORD record
ord-68e790c3af764f7181364644ac90d0b7
Source dataset
uspto-grants-2016_03
Patent number
US09296682B2

Reaction notes

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