Tetrahydrofuran → HCID 178437968, compound

HRID 2095668Notes

Reaction equation

HRID 2095668 reaction equation
[CH2:1]([C:3]1[C:7](I)=[CH:6][N:5]([C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[N:4]=1)[CH3:2].C1COCC1.C([Mg]Cl)(C)C.CO[B:28]1[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]1.[NH4+].[Cl-]>>[CH2:1]([C:3]1[C:7]([B:28]2[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]2)=[CH:6][N:5]([C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[N:4]=1)[CH3:2]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418918HCID 178418918, compoundHCID 178437969HCID 178437969, compound

Product 1

HCID 178437968HCID 178437968, compound

Procedure

To a solution of trans-4-(3-ethyl-4-iodo-1H-pyrazol-1-yl)cyclohexanol (150.0 mg, 0.4685 mmol) in THF (10 mL, 100 mmol) at rt was added 2 M isopropylmagnesium chloride in THF (0.70 mL, 1.4 mmol), and the mixture was stirred for 1 h. The reaction was quenched with 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.31 mL, 1.9 mmol), and allowed to stir at rt for 1 h. Sat. NH4Cl was added, and the organic solvent was removed in vacuo. The material was extracted with DCM and water. 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. stirringto stir at rt for 1 h
  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-51d1a75a62fc49538ad0c4474b160b48
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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