1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → 7-(2-Thienyl)-3-[5-O-(4,4'-dimethoxytrityl)-beta-D-ribofuranosyl]-3H-imidazo[4,5-b]pyridine

HRID 1662292Notes

Reaction equation

HRID 1662292 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([C@@H:15]3[O:21][C@H:20]([CH2:22][OH:23])[C@@H:18]([OH:19])[C@H:16]3[OH:17])[CH:13]=[N:14][C:7]=12.[CH3:24][O:25][C:26]1[CH:47]=[CH:46][C:29]([C:30](Cl)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[CH:28][CH:27]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([C@@H:15]3[O:21][C@H:20]([CH2:22][O:23][C:30]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=4)[C:29]4[CH:28]=[CH:27][C:26]([O:25][CH3:24])=[CH:47][CH:46]=4)[C@@H:18]([OH:19])[C@H:16]3[OH:17])[CH:13]=[N:14][C:7]=12

Participants

5

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 516892Sodium BicarbonateHCID 444333047-(2-Thienyl)-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 674298087-(2-Thienyl)-3-[5-O-(4,4'-dimethoxytrityl)-beta-D-ribofuranosyl]-3H-imidazo[4,5-b]pyridineYield 71.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Compound 11 (99 mg, 0.29 mmol) was azeotroped three times with anhydrous pyridine and then dissolved in pyridine (3.0 ml). To this solution, 4,4′-dimethoxytrityl chloride (106 mg, 0.31 mmol) was added, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into 5% aqueous NaHCO3 and then extracted with ethyl acetate. The organic layer was washed three times with saturated aqueous sodium chloride, dried over Na2SO4, and then evaporated under reduced pressure to remove the solvent. The product was purified by silica gel column chromatography (1% methanol-CH2Cl2) to give Compound 12 (131 mg, 71%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed three times with saturated aqueous sodium chloride
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe product was purified by silica gel column chromatography (1% methanol-CH2Cl2)

Sources & evidence

ORD record
ord-d19a217e87d04e6ab55ce9ef14ec2a6c
Source dataset
uspto-grants-2011_10
Patent number
US08030478B2

Reaction notes

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