5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one → HCID 178517359, compound

HRID 1615359Notes

Reaction equation

HRID 1615359 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][C:9](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](/[CH:18]=[CH:19]/[C:20]2[C:28]3[C:23](=[CH:24][C:25]([CH:29]=O)=[CH:26][CH:27]=3)[NH:22][N:21]=2)[CH:13]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:29][C:25]3[CH:24]=[C:23]4[C:28]([C:20](/[CH:19]=[CH:18]/[C:14]5[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=5)=[N:21][NH:22]4)=[CH:27][CH:26]=3)[C:9](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-oneHCID 86651944(E)-3-(2-(pyridin-3-yl)vinyl)-1H-indazole-6-carbaldehyde

Product 1

HCID 178517359HCID 178517359, compoundYield 84.4%

Procedure

The title compound (E/Z=5:4, 75 mg, 84%) was synthesized as a yellow solid according to the method described for Example A67 (oil temp 75° C., reflux 2 h) using 5-bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (44.5 mg, 0.21 mmol) and (E)-3-(2-(pyridin-3-yl)vinyl)-1H-indazole-6-carbaldehyde (49.8 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) δ 13.64 (s, 0.45H), 13.56 (s, 0.48H), 11.50 (s, 0.91H), 8.94 (s, 0.43H), 8.91 (s, 0.97H), 8.48 (d, J=3.6 Hz, 0.99H), 8.43-8.37 (m, 0.98H), 8.33 (d, J=8.0 Hz, 0.52H), 8.28-8.17 (m, 2.36H), 8.11 (d, J=8.8 Hz, 0.50H), 8.03 (s, 0.56H), 7.94 (s, 1.02H), 7.77-7.69 (2 doublets partially overlapping, J=17.2 Hz, 1.07H, vinylic proton), 7.64-7.54 (m, 1.54H), 7.45-7.41 (2 doublets overlapping, J=8.8 Hz, 1.00H); MS ESI 444.3 [M+H]+, calcd for [C22H14BrN5O+H]+ 444.1.

Workup

  1. customdescribed for Example A67 (oil temp 75° C., reflux 2 h)

Sources & evidence

ORD record
ord-8b5df0837a5b45cb8804863737ca244c
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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