Tetrahydrofuran → HCID 67004424, compound

HRID 2095634Notes

Reaction equation

HRID 2095634 reaction equation
I[C:2]1[C:3]([CH3:12])=[N:4][N:5]([CH2:7][C:8]([CH3:11])([OH:10])[CH3:9])[CH:6]=1.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-]>>[CH3:9][C:8]([OH:10])([CH3:11])[CH2:7][N:5]1[CH:6]=[C:2]([B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[C:3]([CH3:12])=[N:4]1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 67004436HCID 67004436, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 67004424HCID 67004424, compound

Procedure

A solution of 1-(4-iodo-3-methyl-1H-pyrazol-1-yl)-2-methylpropan-2-ol (250.0 mg, 0.8925 mmol) in THF (10 mL, 200 mmol) was added 2 M of isopropylmagnesium chloride in THF (1.339 mL, 2.678 mmol) at rt, and the reaction was allowed to stir for 1 h. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.5850 mL, 3.570 mmol) was then added, and the mixture was stirred at rt for 2 h. 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. stirringthe mixture was stirred at rt for 2 h
  2. customto quench
  3. customthe organic solvent was removed in vacuo
  4. extractionThe material was extracted with DCM and water
  5. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-43e913e98b5b4b878650de83901e3a8b
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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