Tetrahydrofuran → HCID 178431101, compound

HRID 2095669Notes

Reaction equation

HRID 2095669 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([Cl:20])=[C:18](I)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1COCC1.C([Mg]Cl)(C)C.CO[B:34]1[O:38][C:37]([CH3:40])([CH3:39])[C:36]([CH3:42])([CH3:41])[O:35]1.[NH4+].[Cl-]>>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([Cl:20])=[C:18]([B:34]3[O:38][C:37]([CH3:40])([CH3:39])[C:36]([CH3:42])([CH3:41])[O:35]3)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[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 178455355HCID 178455355, compound

Product 1

HCID 178431101HCID 178431101, compound

Procedure

To a solution of 1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-5-chloro-4-iodo-1H-pyrazole (30.0 mg, 0.0680 mmol) in THF (1 mL, 20 mmol) at rt was added 2 M isopropylmagnesium chloride in THF (0.10 mL, 0.20 mmol), and the mixture was stirred for 20 min. The reaction was quenched with 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.045 mL, 0.27 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. 1H NMR (400 MHz, CD3OD): δ=0.12 (s, 6H), 0.93 (s, 9H), 1.33 (s, 8H), 1.46-1.60 (m, 2H), 1.86-2.09 (m, 6H), 3.70-3.82 (m, 1H), 4.38 (ddd, J=10.5, 5.2, 5.1 Hz, 1H), 7.69 (s, 1H).

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-1bb99800df7c486a8389490449650e83
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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