Imidazole → HCID 44470537, compound

HRID 1957888Notes

Reaction equation

HRID 1957888 reaction equation
CN(C=O)C.[N:6]([C:9]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([CH3:20])=[N:14]2)=[N+:7]=[N-:8].N1C=CN=C1.[Si:26](Cl)([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(OCC)(=O)C>[N:6]([C:9]1[CH:18]=[CH:17][C:16]([O:19][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([CH3:20])=[N:14]2)=[N+:7]=[N-:8]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 44470536HCID 44470536, compound

Product 1

HCID 44470537HCID 44470537, compoundYield 1,917.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 100-mL flask was successively loaded with dry DMF (10 mL), 13 (200 mg, 1 mmol), imidazole (68.08 mg, 1 mmol), and tert-butyldiphenylsilyl chloride (302 mg, 1.1 mmol). The solution was stirred at room temperature for 10 h, diluted with ethyl acetate (500 mL), washed with aqueous HCl (0.1 M, 50 mL), brine (100 mL), water (100 mL), dried over Na2SO4 and evaporated under reduced pressure to afford 8.41 g (96%) of protected product as a colorless oil (428 mg, 98%). 1H NMR (500 MHz, CDCl3) δ ppm: 1.19 (s, 9H), 2.33 (s, 3H), 6.98 (d, J=8.5 Hz, 1H), 7.06 (d, J=8.5 Hz, 1H), 7.10 (d, J=8.5 Hz, 1H), 7.38-7.26 (m, 6H), 7.81-7.79 (m, 4H), 8.11 (d, J=8.5 Hz, 1H). 13C NMR (125 MHz, CDCl3) δ ppm: 20.1, 24.3, 26.8, 113.5, 116.7, 120.6, 121.8, 127.3, 128.4, 129.2, 130.6, 134.3, 135.1, 140.9, 148.9, 157.9. HRMS (ESI): calc'd for C26H26N4OSi [M+H]+: 438.1876, found: 438.1879.

Workup

  1. washwashed with aqueous HCl (0.1 M, 50 mL), brine (100 mL), water (100 mL)
  2. dry with materialdried over Na2SO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c05b54ed4a4f40db8c4914b505b4a8a7
Source dataset
uspto-grants-2013_04
Patent number
US08409820B2

Reaction notes

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