Water → HCID 67120045, compound

HRID 1410146Notes

Reaction equation

HRID 1410146 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)[N:7]=[C:6]([CH2:17][CH3:18])[C:5]=1[C:19]#[N:20])[CH3:2].B(Br)(Br)Br.O>C(Cl)Cl>[CH2:21]([N:3]([CH2:1][CH3:2])[C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[N:7]=[C:6]([CH2:17][CH3:18])[C:5]=1[C:19]#[N:20])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67120067HCID 67120067, compound

Product 1

HCID 67120045HCID 67120045, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 5-(diethylamino)-3-ethyl-1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile (39 mg, 0.13 mmol) from above was dissolved in CH2Cl2 (5 mL) and BBr3 (1 M solution in DCM, 1 mL, 1.0 mmol) was added and stirred over night. CH2Cl2 and water were added and the phases were separated, the aqueous phase was again extracted with EtOAc/CH2Cl2 (1:1). The solution was dried using a phase separator and concentrated under reduced pressure. Purification using preparative IIPLC gave 5-(diethylamino)-3-ethyl-1-(4-hydroxyphenyl)-1H-pyrazole-4-carbonitrile (36 mg, 97%).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was again extracted with EtOAc/CH2Cl2 (1:1)
  3. customThe solution was dried
  4. concentrationconcentrated under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-174443f80ee548a48321e83bc8cf5a94
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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