Tetrahydrofuran → HCID 66711033, compound

HRID 1407290Notes

Reaction equation

HRID 1407290 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].Br[C:7]1[C:8](C2C=CC=CC=2)=[N:9][N:10]([C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1.[B:37](OC(C)C)([O:42]C(C)C)[O:38]C(C)C.[CH2:50]1COC[CH2:51]1>>[C:5]1([C:8]2[C:7]([B:37]([OH:42])[OH:38])=[CH:11][N:10]([C:12]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]=2)[CH:51]=[CH:50][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 21531Triisopropyl borateHCID 580724024-Bromo-3-phenyl-1-trityl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 66711033HCID 66711033, compound

Conditions

Temperature
0 °C

Procedure

nBuLi (1.6 M solution in hexane, 25 mL, 40 mmol) was added dropwise at −78° C. to a solution of 4-bromo-3-phenyl-1-trityl-1H-pyrazole (7.96 g, 20.6 mmol) and B(OiPr)3 (6.92 mL, 30 mmol) in THF (75 mL). After stirring for 1 h, the reaction mixture was allowed to warm to 0° C., quenched with saturated NH4Cl aqueous solution, and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with hexane/AcOEt (2/1-0/1) and crystallized from MeOH to give crude (3-phenyl-1-trityl-1H-pyrazol-4-yl)boronic acid (5.73 g) as a white solid.

Workup

  1. customquenched with saturated NH4Cl aqueous solution
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with hexane/AcOEt (2/1-0/1)
  8. customcrystallized from MeOH

Sources & evidence

ORD record
ord-566644390244476f8d602b2aaee1b06e
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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