Sodium Iodide → HCID 22477340, compound

HRID 549053Notes

Reaction equation

HRID 549053 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]([CH3:20])[CH:13]=[C:12]2[C:21]1[N:29]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:23]2[CH:22]=1)C1C=CC=CC=1.[I-].[Na+].C[Si](Cl)(C)C>C(#N)C>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]([CH3:20])[CH:13]=[C:12]2[C:21]1[N:29]([S:30]([C:33]2[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=2)(=[O:32])=[O:31])[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:23]2[CH:22]=1

Participants

5

Reactant 3

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 22477493HCID 22477493, compound

Product 1

HCID 22477340HCID 22477340, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 2-(5-benzyloxy-6-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [6.26 g, Reference Example 13(e)] in acetonitrile (500 mL) was treated with sodium iodide (4.38 g) followed by trimethylsilyl chloride (3.17 mL). The mixture stirred at 40° C. for 3 hours then treated with further portions of sodium iodide (4.38 g) and trimethylsilyl chloride (3.17 mL). After stirring at 40° C. for a further 12 hours the reaction mixture was evaporated. The residue was treated with water (200 mL) and the mixture was extracted three times with ethyl acetate (200 mL). The combined extracts were dried over magnesium sulfate then evaporated. The residual brown foam was triturated with ethyl acetate and diisopropyl ether to give the title compound (3.04 g) as a light brown solid, m.p. 211-214° C. HPLC (METHOD A): RT=9.30 minutes.

Workup

  1. stirringAfter stirring at 40° C. for a further 12 hours the reaction mixture
  2. customwas evaporated
  3. additionThe residue was treated with water (200 mL)
  4. extractionthe mixture was extracted three times with ethyl acetate (200 mL)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customthen evaporated
  7. customThe residual brown foam was triturated with ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-75f93f947f854dc1bbe766277069eb25
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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