Butylboronic Acid → HCID 57658839, compound

HRID 910033Notes

Reaction equation

HRID 910033 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10]CC)=[O:9])=[C:4]([C:15]([C:17]2[CH:18]=[N:19][N:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:21]=2)=[O:16])[CH:3]=1.[CH2:28](B(O)O)[CH2:29][CH2:30][CH3:31]>C1COCC1.O>[CH2:28]([C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([C:15]([C:17]2[CH:18]=[N:19][N:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:21]=2)=[O:16])[CH:3]=1)[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 2

HCID 20479Butylboronic AcidHCID 13507348HCID 13507348, compound

Product 1

HCID 57658839HCID 57658839, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl [4-bromo-2-(1-phenyl-1H-pyrazole-4-carbonyl)phenoxy]acetate (472 mg, 1.1 mmol), 1-butylboronic acid (102 mg, 1.0 mmol) and Pd (dppf)Cl2 (72 mg, 0.05 mmol) in THF (10 mL) and water (1 mL) under argon was refluxed for 24 h. The reaction mixture was extracted with CH2Cl2, the organic phase was filtered through celite and concentrated, and the residue was purified by flash chromatography (SiO2, EtOAc:heptane, 1:10 to 1:1). The purest fraction was concentrated (˜10 mg), and the residue was hydrolysed according to GP3: LC/MS (an 10p8): Rt 2.59 min, m/z 379.1 [M+H]+; 1H NMR (CDCl3): δ 0.88 (t, J=7.5 Hz, 3H), 1.29 (m, 2H), 1.49 (m, 2H), 2.48 (m, 2H), 4.51 (s, 2H), 6.84 (m, 1H), 7.14 (m, 1H), 7.30 (m, 2H), 7.42 (m, 2H), 7.65 (m, 2H), 7.97 (s, 1H), 8.46 (s, 1H).

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2
  2. filtrationthe organic phase was filtered through celite and
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography (SiO2, EtOAc:heptane, 1:10 to 1:1)
  5. concentrationThe purest fraction was concentrated (˜10 mg)

Sources & evidence

ORD record
ord-ded388a13d124c108f0eb73c6d3841f3
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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