m-Chloroperbenzoic acid → HCID 178440859, compound

HRID 1057213Notes

Reaction equation

HRID 1057213 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1/[C:8](/[CH2:31][CH3:32])=[C:9](\[C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])=[CH:22][CH:21]=1)/[C:10]1[CH:11]=[C:12]2[C:16](=[C:17]([F:19])[CH:18]=1)[NH:15][N:14]=[CH:13]2.C1C=C(Cl)C=C(C(OO)=[O:41])C=1>ClCCl>[C:28](/[CH:27]=[CH:26]/[C:23]1[CH:24]=[CH:25][C:20](/[C:9](/[C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([F:19])[CH:18]=2)[NH:15][N:14]=[CH:13]3)=[C:8](\[C:7]2[CH:6]=[CH:5][N+:4]([O-:41])=[CH:3][C:2]=2[Cl:1])/[CH2:31][CH3:32])=[CH:21][CH:22]=1)([OH:30])=[O:29]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 66803320HCID 66803320, compound2×

Product 1

HCID 178440859HCID 178440859, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (E)-3-(4-((E)-2-(3-chloropyridin-4-yl)-1-(7-fluoro-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylic acid (14.1 mg, 0.031 mmol, Compound 245), mCPBA (11 mg, 0.048 mmol), and dichloromethane (0.5 mL) was stirred vigorously for 15 h. Additional starting material (20 mg, 0.045 mmol) and mCPBA (15 mg, 0.065 mmol) were added and stirring was continued for 3 d. The reaction was concentrated and then purified by reverse-phase HPLC(CH3CN, H2O, TFA) to give 4-((E)-1-(4-((E)-2-carboxyvinyl)phenyl)-1-(7-fluoro-1H-indazol-5-yl)but-1-en-2-yl)-3-chloropyridine-1-oxide. 1H NMR (400 MHz, DMSO-d6): δ 8.44 (d, 1H), 8.25 (d, 1H), 8.16 (dd, 2H), 7.56 (s, 1H), 7.50-7.42 (m, 4H), 7.05-6.96 (m, 3H), 6.43 (d, 1H), 2.41 (q, 2H), 0.94 (t, 3H); LCMS: 464.0 (M+H)+.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitwas continued for 3 d
  4. concentrationThe reaction was concentrated
  5. custompurified by reverse-phase HPLC(CH3CN, H2O, TFA)

Sources & evidence

ORD record
ord-38982e5a2bdd414db33587acec087f87
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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