1,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-one → HCID 178517370, compound

HRID 1615283Notes

Reaction equation

HRID 1615283 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][C:2]1=[O:10].[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH:20]=O)[CH:18]=2)[CH:13]=[N:12]1>CO.N1CCCCC1>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17](/[CH:20]=[C:3]3/[C:2](=[O:10])[NH:1][C:5]4[C:4]/3=[CH:9][CH:8]=[CH:7][N:6]=4)[CH:18]=2)[CH:13]=[N:12]1

Participants

5

Reactant 2

HCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-oneHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178517370HCID 178517370, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 1H-pyrrolo[2,3-b]pyridin-2(3H)-one (26.8 mg, 0.2 mmol) and 1H-indazole-6-carbaldehyde (29.2 mg, 0.2 mmol) in MeOH (2 mL) was added 1 drop of piperidine via syringe needle. The resulting mixture was refluxed for 2 h (oil temp. 70° C.) and then cooled to rt. The resulting precipitate was collected by suction filtration to give the title compound as a yellow solid (37 mg, 71%). 1H NMR (400 MHz, DMSO-d6) δ 13.31 (s, 1H, NH), 11.25 (s, 1H, NH), 8.16 (s, 1H), 8.10 (d, J=5.2 Hz, 1H), 7.93-7.87 (m, 4H), 7.44 (d, J=8.8 Hz, 1H), 6.90 (dd, J=7.6 Hz, 5.6 Hz, 1H); MS ESI 263.0 [M+H]+, calcd for [C15H10N4O+H]+ 263.1.

Workup

  1. temperaturecooled to rt
  2. filtrationThe resulting precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-d84c62219d6c41c0a43857e42745e1ac
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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