Tetrahydrofuran → HCID 178434088, compound

HRID 2095655Notes

Reaction equation

HRID 2095655 reaction equation
I[C:2]1[C:3]([CH3:14])=[N:4][N:5]([C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=1.C1COCC1.C([Mg]Cl)(C)C.CO[B:27]1[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]1>>[CH3:14][C:3]1[C:2]([B:27]2[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]2)=[CH:6][N:5]([C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[N:4]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418918HCID 178418918, compoundHCID 178434089HCID 178434089, compound

Product 1

HCID 178434088HCID 178434088, compound

Procedure

To a solution of trans-4-(4-iodo-3-methyl-1H-pyrazol-1-yl)cyclohexanol (150.0 mg, 0.4900 mmol) in THF (9 mL, 100 mmol) was added 2 M isopropylmagnesium chloride in THF (0.7349 mL, 1.470 mmol) at rt, and the mixture was stirred for 30 min. 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.3212 mL, 1.960 mmol) was added, and the mixture stirred at rt for 2 h. The reaction was quenched with sat. NH4Cl, 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 clear oil.

Workup

  1. stirringthe mixture stirred at rt for 2 h
  2. customThe reaction was quenched with sat. NH4Cl
  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-4e10350a800949b49151ce1665dd2077
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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