Water → HCID 136340259, compound

HRID 1466611Notes

Reaction equation

HRID 1466611 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24]CC2C=CC(OC)=CC=2)=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[CH:10][C:9]=2[N+:21]([O-:23])=[O:22])[CH:7]=1.O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[N:11]=[CH:10][C:9]=2[N+:21]([O-:23])=[O:22])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 66850887HCID 66850887, compound

Product 1

HCID 136340259HCID 136340259, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(5-chloro-2-(4-methoxybenzyloxy)phenyl)-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (prepared according to the procedure described for Example 14) (1.193 g, 2.434 mmol) in 17 mL dichloromethane was added 3 mL water followed by dichlorodicyanoquinone (1.2208 g). The reaction was stirred at room temperature for 48 hours, and then additional Dichlorodicyanoquinone (0.4946 g) was added. After an additional 24 hours, the reaction was poured into saturated aqueous sodium bicarbonate and extracted with dichloromethane. The organic portion was dried over magnesium sulfate and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (0 to 35% ethyl acetate in heptanes) to yield 745.2 mg (83%) of 4-chloro-2-(4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)phenol. LCMS (ESI) m+H=270.2; 1H NMR (400 MHz, DMSO-d6) δ: 10.47 (s, 1H), 8.44 (s, 1H), 7.47 (d, J=2.6, 1H), 7.43 (dd, J=8.8, 2.7, 1H), 7.00 (d, J=8.8, 1H), 5.30 (dd, J=65.1, 10.8, 2H), 3.42 (t, J=8.1, 2H), 0.74 (t, 2H), −0.08 (s, 9H).

Workup

  1. waitAfter an additional 24 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic portion was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude product was purified via flash chromatography on silica gel (0 to 35% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-6bd0495d2e3b437799c07fa51e0dc66b
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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