HCID 68159448, compound → HCID 68159624, compound

HRID 341025Notes

Reaction equation

HRID 341025 reaction equation
[C@@H:1]1([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][C:17]([C:18]4[N:19](S(N(C)C)(=O)=O)[CH:20]=[CH:21][N:22]=4)=[C:12]3[CH:11]=[CH:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1>C(O)(=O)C>[C@@H:1]1([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][C:17]([C:18]4[NH:19][CH:20]=[CH:21][N:22]=4)=[C:12]3[CH:11]=[CH:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1

Participants

3

Reactant 1

HCID 68159448HCID 68159448, compound

Product 1

HCID 68159624HCID 68159624, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

N-Dimethylaminosulfonyl-2-(tributylstannyl)imidazole (930 mg, 2.0 mmol) was added to a solution of 1-[2-deoxy-3,5-di-O-(toluoyl)-β-D-ribofuranosyl]-4-iodo-pyrrolo[2,3-b]pyridine (596 mg, 1.0 mmol), lithium chloride (42 mg, 1.0 mmol), and tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol) in dioxane (10 mL), followed by stirring at 120° C. for 4 hr. The reaction solution was concentrated and was then purified with a silica gel column, and methanolic ammonia (30 mL) was added thereto. The resulting mixture was stirred at room temperature for 24 hr. The reaction solution was concentrated and purified with a silica gel column and then with HPLC to yield 218 mg (54%, second stage yield) of 1-(2-deoxy-β-D-ribofuranosyl)-4-(N-dimethylaminosulfonyl-2-imidazolyl)-pyrrolo[2,3-b]pyridine. 1-(2-Deoxy-β-D-ribofuranosyl)-4-(N-dimethylaminosulfonyl-2-imidazolyl)-pyrrolo[2,3-b]pyridine (200 mg, 0.49 mmol) was dissolved in 80% acetic acid, followed by stirring at 60° C. for 3 hr. The reaction solution was concentrated, and aqueous ammonia was added thereto for further concentration. Subsequently, 1-(2-deoxy-β-D-ribofuranosyl)-4-(2-imidazolyl)-pyrrolo[2,3-b]pyridine (dDia: 109 mg, 74%) was obtained through purification by HPLC.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionaqueous ammonia was added
  3. concentrationfor further concentration

Sources & evidence

ORD record
ord-ca8afd61084548548e7b6750d40855c0
Source dataset
uspto-grants-2014_11
Patent number
US08895712B2

Reaction notes

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