Tetrahydrofuran → HCID 67004713, compound

HRID 2095635Notes

Reaction equation

HRID 2095635 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]([CH3:12])([OH:11])[CH3:10])[C:6]=1[CH3:7].C1COCC1.C([Mg]Cl)(C)C.CO[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1.[NH4+].[Cl-]>>[CH3:10][C:9]([OH:11])([CH3:12])[CH2:8][N:5]1[C:6]([CH3:7])=[C:2]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH:3]=[N:4]1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 67004232HCID 67004232, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 67004713HCID 67004713, compound

Procedure

A solution of 1-(4-iodo-5-methyl-1H-pyrazol-1-yl)-2-methylpropan-2-ol (150.0 mg, 0.5355 mmol) in THF (8 mL, 100 mmol) was added 2 M isopropylmagnesium chloride in THF (0.80 mL, 1.6 mmol) at 0° C., and the reaction was allowed to warm to rt over 30 min. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.35 mL, 2.1 mmol) was then added, and the mixture was stirred at rt overnight. Sat. NH4Cl was added to quench, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was concentrated in vacuo to afford the title compound as a white solid. The material was used in the next step without further purification.

Workup

  1. customto quench
  2. customthe organic solvent was removed in vacuo
  3. extractionThe material was extracted with DCM and water
  4. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-3bb1a9bc86dd4c38962110de478cbc25
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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