m-Chloroperbenzoic acid → HCID 178487093, compound

HRID 1615299Notes

Reaction equation

HRID 1615299 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])/[C:6]/2=[CH:13]/[C:14]1[CH:22]=[C:21]2[C:17]([C:18](/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[N:19][NH:20]2)=[CH:16][CH:15]=1.C1C=C(Cl)C=C(C(OO)=[O:39])C=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])/[C:6]/2=[CH:13]/[C:14]1[CH:22]=[C:21]2[C:17]([C:18](/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N+:26]=3[O-:39])=[N:19][NH:20]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178487092HCID 178487092, compound

Product 1

HCID 178487093HCID 178487093, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with (E)-5-methoxy-3-((3-((E)-2-(pyridin-2-yl)vinyl)-1H-indazol-6-yl)methylene)indolin-2-one (25 mg, 0.063 mmol), mCPBA (13 mg, 0.076 mmol), and dichloromethane (4 mL). The reaction was stirred at rt for 24 hrs. Solvent was removed in vacuo and the residue was loaded onto a silica gel column. Elution with 90:10 CH2Cl2/MeOH gave 9 mg (35%) of the title compound as an orange solid. 1H NMR (400 MHz, CD3OD) δ 8.41 (d, J=6.0 Hz, 1H), 8.31 (d, J=8.5 Hz, 1H), 8.19 (d, J=16.3 Hz, 1H), 8.14 (d, J=8.0 Hz, 1H), 8.04 (d, J=17.1 Hz, 1H), 7.91 (d, J=16.1 Hz, 2H), 7.67-7.60 (m, 2H), 7.47-7.43 (m, 1H), 7.25 (s, 1H), 6.85 (s, 2H), 3.64 (s, 3H); MS ESI 411.2 [M+H]+, calcd for [C24H18N4O3+H]+ 411.14.

Workup

  1. customSolvent was removed in vacuo
  2. washElution with 90:10 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-cf1afd19db7f4f08ad4746b4f8b8362e
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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