Trimethylsilyl iodide → HCID 54689891, compound

HRID 1244102Notes

Reaction equation

HRID 1244102 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([OH:24])=[CH:21][C:20](=[O:25])[NH:19][C:18]=3[S:17][CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.I[Si](C)(C)C>C(Cl)Cl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:23]3[C:22]([OH:24])=[CH:21][C:20](=[O:25])[NH:19][C:18]=3[S:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 54689835HCID 54689835, compound

Product 1

HCID 54689891HCID 54689891, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 349 mg (1.00 mmol) of 3-(4-benzyloxy-phenyl)-4-hydroxy-7H-thieno[2,3-b]pyridin-6-one from Example 7d in 10 mL of CH2Cl2 was added 0.7 mL (4.9 mmol) of iodotrimethylsilane. The reaction was stirred at ambient temperature for 48 h, then concentrated in vacuo. The residue was suspended in 10 mL of water, and 5% NaHSO3(aq.) was added to discharge the I2 color. The insoluble material was filtered, washed with water, then diethyl ether, and dried on the filter to give 183 mg (70%) of a tan solid. MS (ESI) m/e 259.9, (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 5.69 (s, 1H) 6.72 (m, 2H) 6.85 (s, 1H) 7.24 (m, 2H) 9.39 (s, 1H) 10.79 (s, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. addition5% NaHSO3(aq.) was added
  3. filtrationThe insoluble material was filtered
  4. washwashed with water
  5. dry with materialdiethyl ether, and dried on the
  6. filtrationfilter

Sources & evidence

ORD record
ord-ce6f17d3745c4991bd48d9c67237a50a
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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