Imidazole → HCID 22663837, compound

HRID 392405Notes

Reaction equation

HRID 392405 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C1COCC1>[Si:21]([O:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:7]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 506617HCID 506617, compound

Product 1

HCID 22663837HCID 22663837, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(4-hydroxyphenyl)pyridin-3-ylmethylamine (1.0 equiv.) in THF (0.1 M) was cooled to 0° C. and treated with imidazole (1.0 equiv.) and t-butyldimethylsilyl chloride (1.1 equiv.). The reaction was warmed to ambient temperature and stirred overnight. The THF was removed in vacuo. The residue was dissolved in ethyl acetate and washed with 0.1 N HCl, saturated aqueous NaHCO3, water, and brine. The residue was purified via preparative HPLC eluting with 80:20 to 68:32 DCM/ethyl acetate to give N-(4-(t-butyldimethylsilyloxy)phenyl) pyridin-3-ylmethylamine. Anal Calcd for C18H26N2OSi: C, 68.74; H, 8.33; N, 8.91. Found: C, 68.62; H, 8.28; N, 8.74. 1H NMR (400 MHz) 0.15 (6H, s), 0.96 (9H, s), 3.77 (1H, bs), 4.30 (2H, s), 6.53 (2H, m), 6.70 (2H, m), 7.26 (1H, m), 7.70 (1H, td, J=1.9, 7.7 Hz), 8.53(1H, dd, J=1.4, 4.6 Hz), 8.62 (1H, d, J=1.6 Hz). MS found 315.2 [M+H]+

Workup

  1. customThe THF was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 0.1 N HCl, saturated aqueous NaHCO3, water, and brine
  4. customThe residue was purified via preparative HPLC
  5. washeluting with 80:20 to 68:32 DCM/ethyl acetate

Sources & evidence

ORD record
ord-c366e4ca2932418a832cf2630afc5c5e
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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