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Tetrahydrofuran → HCID 178421687, compound

HRID 2095677
Notes
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Reaction equation

HRID 2095677 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([CH3:20])=[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]([CH3:20])=[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 109757592-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418918HCID 178418918, compoundHCID 178429782HCID 178429782, compound

Product 1

HCID 178421687HCID 178421687, compound

Procedure

To a solution of 1-(cis-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-4-iodo-5-methyl-1H-pyrazole (870.0 mg, 2.069 mmol) in THF (20 mL, 200 mmol) at rt was added 1.3 M of isopropylmagnesium chloride in THF (6.367 mL, 8.278 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 (1.696 mL, 10.35 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 yellow solid. 1H NMR (400 MHz, CD3OD): δ=0.12 (s, 6H), 0.97 (s, 9H), 1.33 (s, 9H), 1.60-1.75 (m, 4H), 1.83-1.92 (m, 2H), 2.32-2.40 (m, 2H), 2.47 (s, 3H), 4.07-4.21 (m, 2H), 7.58 (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-eb85f11cbdf34a9db6489e575028b162
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08445510B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes