1,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-one → HCID 178517371, compound

HRID 1615284Notes

Reaction equation

HRID 1615284 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][C:16]([CH:20]=O)=[CH:17][CH:18]=2)[CH:13]=[N:12]1>>[NH:11]1[C:19]2[C:14](=[CH:15][C:16](/[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:17][CH:18]=2)[CH:13]=[N:12]1

Participants

3

Reactant 2

HCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-oneHCID 212506441H-Indazole-5-carboxaldehyde

Product 1

HCID 178517371HCID 178517371, compoundYield 95.3%

Procedure

The title compound (50 mg, 95%) was synthesized as an orange solid according to the method described for Example A67 using 1H-pyrrolo[2,3-b]pyridin-2(3H)-one (26.8 mg, 0.2 mmol) and 1H-indazole-5-carbaldehyde (29.2 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.36 (s, 1H, NH), 11.20 (s, 1H, NH), 8.21 (s, 2H), 8.09 (d, J=5.2 Hz, 1H), 7.94 (d, J=8.0 Hz, 1H), 7.89 (s, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.68 (d, J=8.4 Hz, 1H), 6.91 (dd, J=8.0 Hz, 5.6 Hz, 1H); MS ESI 263.0 [M+H]+, calcd for [C15H10N4O+H]+ 263.1.

Sources & evidence

ORD record
ord-79cae1a2b58a4e6a825d83122d23ae88
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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