Water → HCID 86719368, compound

HRID 1844501Notes

Reaction equation

HRID 1844501 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:11]=[N:10]1.C([O-])([O-])=O.[K+].[K+].[CH:26]1[CH:31]=[CH:30][C:29]([CH2:32][O:33][C:34](Cl)=[O:35])=[CH:28][CH:27]=1.O>ClCCl>[CH2:32]([O:33][C:34]([NH:8][C:6]1[CH:5]=[CH:4][C:3]([N:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:11]=[N:10]2)=[C:2]([F:1])[CH:7]=1)=[O:35])[C:29]1[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 86719366HCID 86719366, compound

Product 1

HCID 86719368HCID 86719368, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg of 2-(1-(2-fluoro-4-aminophenyl)-1H-pyrazol-4-yl)pyridine (25f) was dissolved in 5 mL dichloromethane, with addition of 194.3 mg K2CO3. Then, 990 μL Cbz-Cl was slowly dropped into the resultant mixture maintained in an ice bath. After completion of the addition, the ice bath was removed. The reaction mixture was warmed naturally to room temperature and reacted for 2 hours. TLC monitoring was performed to determine the completion of the reaction, after which water was added into the reaction solution. The mixture was extracted with dichloromethane for three times. The combined organic phase was dried and rotary evaporated. The residue obtained was repeatedly washed with petroleum ether until the excess Cbz-Cl was completely removed, thereby affording 260 mg of a light yellow solid, with a yield of 95.1%.

Workup

  1. temperaturemaintained in an ice bath
  2. additionAfter completion of the addition
  3. customthe ice bath was removed
  4. customreacted for 2 hours
  5. customthe completion of the reaction
  6. extractionThe mixture was extracted with dichloromethane for three times
  7. customThe combined organic phase was dried
  8. customThe residue obtained
  9. washwas repeatedly washed with petroleum ether until the excess Cbz-Cl
  10. customwas completely removed

Sources & evidence

ORD record
ord-209d8bb89277472b9317fb8f44ff70cb
Source dataset
uspto-grants-2015_02
Patent number
US08946436B2

Reaction notes

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