Dichloromethane → HCID 54679007, compound

HRID 1244109Notes

Reaction equation

HRID 1244109 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:22]([OH:24])=C[C:20](=[O:25])[NH:19][C:18]=3[S:17][CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[Cl:26]N1C(=O)CCC1=O.I[Si](C)(C)C.[CH2:39]([Cl:41])Cl>>[Cl:26][C:16]1[S:17][C:18]2[NH:19][C:20](=[O:25])[C:39]([Cl:41])=[C:22]([OH:24])[C:23]=2[C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 85247Trimethylsilyl iodideHCID 54689835HCID 54689835, compound

Product 1

HCID 54679007HCID 54679007, compoundYield 34%

Procedure

To a suspension of 50 mg (0.14 mmol) of 3-(4-benzyloxy-phenyl)-4-hydroxy-7H-thieno[2,3-b]pyridin-6-one from Example 7D in 2 mL of CH2Cl2 was added 38 mg (0.28 mmol) of N-chlorosuccinimide. The suspension became a homogeneous solution, and was stirred open to the air while the solvent was allowed to evaporate to dryness over two days. The residue was redissolved in 2 mL of CH2Cl2, and 100 μL (0.72 mmol) of iodotrimethylsilane was added. After 18 h, the reaction was concentrated in vacuo. The residue was dissolved in ethyl acetate (5 mL) and extracted with 5% NaHSO3(aq.) (1×2 mL) to discharge the 12 color, then with brine (1×2 mL), dried over MgSO4, filtered, and concentrated to an oil. This was purified via reverse phase HPLC (0 to 70% CH3CN/0.1% aq. TFA gradient) to give 16 mg (34%) of a solid as the titled compound. MS (ESI) m/e 327.8, (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 6.79 (m, 2H) 7.15 (m, 2H) 9.54 (s, 1H) 10.84 (s, 1H) 12.40 (bs, 1H).

Workup

  1. customto evaporate to dryness over two days
  2. dissolutionThe residue was redissolved in 2 mL of CH2Cl2
  3. concentrationthe reaction was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (5 mL)
  5. extractionextracted with 5% NaHSO3(aq.) (1×2 mL)
  6. dry with materialwith brine (1×2 mL), dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThis was purified via reverse phase HPLC (0 to 70% CH3CN/0.1% aq. TFA gradient)

Sources & evidence

ORD record
ord-8705b10d99c742fcbb39c262c4bfd3ed
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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