Tetrahydrofuran → HCID 178421685, compound

HRID 2095724Notes

Reaction equation

HRID 2095724 reaction equation
I[C:2]1[CH:3]=[N:4][N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]2)[C:6]=1[CH3:7].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.[NH4+].[Cl-]>>[CH3:7][C:6]1[N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]2)[N:4]=[CH:3][C:2]=1[B:27]1[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418918HCID 178418918, compoundHCID 178429779HCID 178429779, compound

Product 1

HCID 178421685HCID 178421685, compound

Procedure

To a solution of trans-4-(4-iodo-5-methyl-1H-pyrazol-1-yl)cyclohexanamine (170.0 mg, 0.5571 mmol) in THF (4 mL, 60 mmol) at rt was added 1.3 M of isopropylmagnesium chloride in THF (1.7 mL, 2.2 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 (0.46 mL, 2.8 mmol), and allowed to stir at rt for 2 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, and was used without further purification.

Workup

  1. stirringto stir at rt for 2 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-86a3d80a72584e76ae763488e16a7b18
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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