Imidazole → HCID 178455351, compound

HRID 389443Notes

Reaction equation

HRID 389443 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:14]([O:13][C@H:10]1[CH2:9][CH2:8][C@H:7]([N:5]2[CH:6]=[C:2]([I:1])[CH:3]=[N:4]2)[CH2:12][CH2:11]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178521568HCID 178521568, compound

Product 1

HCID 178455351HCID 178455351, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of trans-4-(4-iodo-1H-pyrazol-1-yl)-cyclohexanol (1.00 g, 3.42 mmol), tert-butyldimethylsilyl chloride (1.03 g, 6.85 mmol), and DMAP (80 mg, 0.7 mmol), 1H-imidazole (699 mg, 10.3 mmol) in DCM (20 mL) was stirred RT for 20 min. The mixture was diluted with DCM and washed with saturated NaHCO3. The organic layer was dry-loaded onto silica gel. Flash chromatography (3% EtOAc:hexanes) afforded 1.37 g (98%) of the title compound as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 0.05 (s, 6 H), 0.86 (s, 9 H), 1.33-1.47 (m, 2 H), 1.70-1.91 (m, 4 H), 1.96 (d, J=11.9 Hz, 2 H), 3.58-3.75 (m, 1 H), 4.11-4.21 (m, 1 H), 7.49 (s, 1 H), 7.92 (s, 1 H); MS (ESI): 407.05 [M+H]+; HPLC tR=3.22 min.

Workup

  1. washwashed with saturated NaHCO3

Sources & evidence

ORD record
ord-788346ad6e9240aa95c10241dc0c81a3
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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