5-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one → HCID 178517173, compound

HRID 1615354Notes

Reaction equation

HRID 1615354 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=O)[CH:19]=2)[CH:14]=[N:13]1>>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18](/[CH:21]=[C:8]3/[C:9](=[O:11])[NH:10][C:5]4[C:6]/3=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[CH:19]=2)[CH:14]=[N:13]1

Participants

3

Reactant 2

HCID 106546885-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-oneHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178517173HCID 178517173, compoundYield 67.4%

Procedure

The title compound (40 mg, 67%) was synthesized as an orange solid according to the method described for Example A67 (oil temp 75° C., reflux 30 min) using 5-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (33.7 mg, 0.2 mmol) and 1H-indazole-6-carbaldehyde (29.2 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.56 (s, 1H), 10.90 (s, 1H), 8.93 (s, 1H), 8.37 (d, J=8.4 Hz, 1H), 8.17 (s, 1H), 7.93 (s, 1H), 7.89 (d, J=8.4 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.35 (d, J=8.0 Hz, 1H); MS ESI 297.0 [M+H]+, calcd for [C15H9ClN4O+H]+ 297.1.

Workup

  1. customdescribed for Example A67 (oil temp 75° C., reflux 30 min)

Sources & evidence

ORD record
ord-e345e3e30aff4d39bdc8ce3617b070f1
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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