Pyridine → HCID 10349022, compound

HRID 486205Notes

Reaction equation

HRID 486205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[C:11](=[O:42])[CH:12]([CH:15]([OH:41])[C:16]3[N:17]=[CH:18][N:19]([C:22]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:20]=3[CH3:21])[CH2:13][CH2:14][C:6]1=[C:5]2[CH3:43].N1C=CC=CC=1.[C:50](OC(=O)C)(=[O:52])[CH3:51]>ClCCl>[C:50]([O:41][CH:15]([C:16]1[N:17]=[CH:18][N:19]([C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:20]=1[CH3:21])[CH:12]1[C:11](=[O:42])[N:7]2[C:8]3[C:4]([C:5]([CH3:43])=[C:6]2[CH2:14][CH2:13]1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)(=[O:52])[CH3:51]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10031247HCID 10031247, compound

Product 1

HCID 10349022HCID 10349022, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-8,9-dihydro-7-[(hydroxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one (1.64 g) in dichloromethane (32 ml) were added pyridine (0.83 ml) and acetic anhydride (0.53 ml). The solution was refluxed for 24 hours. After being cooled, the solution was washed with water twice and brine, dried over sodium sulfate, and evaporated, to give 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-2-chloro-8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one (1.49 g).

Workup

  1. temperatureThe solution was refluxed for 24 hours
  2. temperatureAfter being cooled
  3. washthe solution was washed with water twice
  4. dry with materialbrine, dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-19dffedeb2ed46b48221f61f20ccc941
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Reaction notes

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