m-Chloroperbenzoic acid → Ethyl 3-[(2-cyanophenyl)amino]-7-[4-(methylsulfinyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylate

HRID 30431Notes

Reaction equation

HRID 30431 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[C:18]2[CH:17]=[CH:16][C:15](=[O:19])[N:14]([C:20]3[CH:25]=[CH:24][C:23]([S:26][CH3:27])=[CH:22][CH:21]=3)[C:13]=2[S:12][C:11]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])#[N:2].ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[C:18]2[CH:17]=[CH:16][C:15](=[O:19])[N:14]([C:20]3[CH:21]=[CH:22][C:23]([S:26]([CH3:27])=[O:41])=[CH:24][CH:25]=3)[C:13]=2[S:12][C:11]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68526060HCID 68526060, compound

Product 1

HCID 68454333Ethyl 3-[(2-cyanophenyl)amino]-7-[4-(methylsulfinyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-2-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of Example 78 (1.0 g, 2.17 mmol) and m-chloroperbenzoic acid (534 mg, 1 eq) in DCM (50 mL) was stirred at r.t. for 2 h. The mixture was diluted with DCM, washed with NaHCO3 aq, dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (silica, 50% EtOAc in DCM) gave the title compound (850 mg, 82%). δH (CDCl3) 8.80 (1H, s), 8.12-7.70 (2H, m), 7.65-7.53 (3H, m), 7.50 (1H, t, J 7.4 Hz), 7.27 (1H, d, J 9.8 Hz), 7.17-7.09 (2H, m), 6.45 (1H, d, J 9.8 Hz), 4.28 (2H, q, J 7.1 Hz), 2.83 (3H, s), 1.30 (3H, t, J 7.1 Hz). LCMS (ES+) RT 3.16 minutes, 478 (M+H)+.

Workup

  1. washwashed with NaHCO3 aq
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (silica, 50% EtOAc in DCM)

Sources & evidence

ORD record
ord-1ac5272574f741c3b8cba9aa8722dfaa
Source dataset
uspto-grants-2008_09
Patent number
US07423047B2

Reaction notes

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