Potassium Carbonate → HCID 22256626, compound

HRID 1611534Notes

Reaction equation

HRID 1611534 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH:11][C:12]1[C:17]([C:18]#[N:19])=[CH:16][N:15]=[C:14]2[CH:20]=[C:21]([C:23]#[C:24][Si](C)(C)C)[S:22][C:13]=12.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH:11][C:12]1[C:17]([C:18]#[N:19])=[CH:16][N:15]=[C:14]2[CH:20]=[C:21]([C:23]#[CH:24])[S:22][C:13]=12

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22256668HCID 22256668, compound

Product 1

HCID 22256626HCID 22256626, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the suspension of 7-[(2,4-dichloro-5-methoxyphenyl)amino]-2-[(trimethylsilyl)ethynyl]thieno[3,2-b]pyridine-6-carbonitrile (97 mg, 0.22 mmol) in 10 mL of methanol is added potassium carbonate (46 mg, 0.33 mmol) The mixture is stirred at room temperature for 30 minutes, concentrated in vacuo and then partitioned between water and ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash column chromatography eluting with 1:1 ethyl acetate:hexane to provide 38 mg of 7-[(2,4-dichloro-5-methoxyphenyl)amino]-2-ethynylthieno[3,2-b]pyridine-6-carbonitrile as white crystals, mp 198-200° C.; 1H NMR (DMSO-d6) δ 3.85 (s, 3H), 5.01 (s, 1H), 7.38 (s, 1H), 7.72 (s, 1H), 7.79 (s, 1H), 8.63 (s, 1H), 9.85 (s, 1H); MS 372.0 (M−H)−.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography
  7. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-982bb444e3dc48fe981b7c90bd93a60c
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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