Imidazole → HCID 178434091, compound

HRID 2095632Notes

Reaction equation

HRID 2095632 reaction equation
[I:1][C:2]1[C:3]([CH3:15])=[N:4][N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10][CH2:9]2)[C:6]=1[CH3:7].[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1.C(Cl)Cl>CN(C)C1C=CN=CC=1>[Si:16]([O:14][C@H:11]1[CH2:12][CH2:13][C@H:8]([N:5]2[C:6]([CH3:7])=[C:2]([I:1])[C:3]([CH3:15])=[N:4]2)[CH2:9][CH2:10]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 178434090HCID 178434090, compound

Product 1

HCID 178434091HCID 178434091, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of trans-4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)cyclohexanol (206.0 mg, 0.6434 mmol), tert-butyldimethylsilyl chloride (0.194 g, 1.29 mmol), 4-dimethylaminopyridine (20 mg, 0.1 mmol), imidazole (131 mg, 1.93 mmol) and DCM (4 mL, 60 mmol) was stirred at rt for 20 min. The material was transferred to a separatory funnel, extracting with DCM and sat. NaHCO3. The organic layer was dry-loaded onto silica gel for column chromatography, eluting with 3% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a clear oil. MS (ES+): m/z=435.14 (100) [MH+]. HPLC: tR=2.26 min (polar—3 min, UPLC-ACQUITY).

Workup

  1. customThe material was transferred to a separatory funnel
  2. extractionextracting with DCM and sat. NaHCO3
  3. washeluting with 3% EtOAc/hexanes
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-a634e5163c8842a0b136b1f00951aa35
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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