5-fluoro-1,3-dihydro-2H-indol-2-one → HCID 178517180, compound

HRID 2281693Notes

Reaction equation

HRID 2281693 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[I:12][C:13]1[C:21]2[C:16](=[CH:17][C:18]([CH:22]=O)=[CH:19][CH:20]=2)[NH:15][N:14]=1>N1CCCCC1.CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:22]\[C:18]1[CH:17]=[C:16]2[C:21]([C:13]([I:12])=[N:14][NH:15]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 178519327HCID 178519327, compound

Product 1

HCID 178517180HCID 178517180, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A round bottom flask was charged with 5-fluoroindolin-2-one (100 mg, 0.661 mmol), 3-iodo-1H-indazole-6-carbaldehyde (180 mg, 0.661 mmol), piperidine (13 uL, 0.027 mmol) and methanol (7.5 mL). The reaction was then heated to 60° C. for 3 h prior to cooling the reaction mass to room temperature. Filtration and washing with methanol (0.50 mL×2) gave the title compound as a yellow solid (260 mg, 96%). 1H NMR (400 MHz, DMSO-d6) δ 13.82 (s, 1H), 10.72 (s, 1H), 9.00 (s, 1H), 8.06 (s, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.71 (s, J=8.8 Hz, 1H), 7.48 (d, J=8.8 Hz, 1H), 7.07-7.02 (m, 1H), 6.81 (d, J=4.4 Hz, 1H).

Workup

  1. temperatureto cooling the reaction mass to room temperature
  2. filtrationFiltration
  3. washwashing with methanol (0.50 mL×2)

Sources & evidence

ORD record
ord-b076c6975987448fa8c73298ddb21da9
Source dataset
uspto-grants-2015_09
Patent number
US09139563B2

Reaction notes

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