Imidazole → 1-[3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-4-iodo-1H-pyrazole

HRID 1947844Notes

Reaction equation

HRID 1947844 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:10][CH:9]([OH:11])[CH2:8]2)[CH:6]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:20]([Si:17]([CH3:19])([CH3:18])[O:11][CH:9]1[CH2:8][CH:7]([N:5]2[CH:6]=[C:2]([I:1])[CH:3]=[N:4]2)[CH2:10]1)([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 672540253-(4-Iodo-1H-pyrazol-1-yl)cyclobutanol2×

Product 1

HCID 672531081-[3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-4-iodo-1H-pyrazoleYield 55%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-Iodo-pyrazol-1-yl)-cyclobutanol (Compound 100C, 75.00 mg, 0.2840 mmol), 4-dimethylaminopyridine (6.940 mg, 0.05680 mmol), 1H-imidazole (58.01 mg, 0.8521 mmol), tert-butyldimethylsilyl chloride (0.08562 g, 0.5680 mmol) and DCM (4 mL) were stirred at room temperature for 20 minutes. The material was transferred to a separatory funnel extracting with DCM washing with aqueous saturated NaHCO3. The organic layer was dry-loaded on silica for column chromatography eluting with 3% EtOAc in hexanes to afford 59 mg (55% yield) of the title compound as colorless oil. MS (ES+): m/z 378.94 (100) [MH+]; HPLC: tR=4.35 min (Polar—5 min, ZQ3).

Workup

  1. customThe material was transferred to a separatory funnel
  2. extractionextracting with DCM washing with aqueous saturated NaHCO3
  3. washeluting with 3% EtOAc in hexanes

Sources & evidence

ORD record
ord-0c036ffb2b694f139061f762e8d42666
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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