5-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one → HCID 178517172, compound
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.[N:12]1[CH:17]=[CH:16][C:15](/[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:14][CH:13]=1>>[Cl:1][C:2]1[N:7]=[C:6]2[C:8](=[CH:29][C:25]3[CH:24]=[C:23]4[C:28]([C:20](/[CH:19]=[CH:18]/[C:15]5[CH:14]=[CH:13][N:12]=[CH:17][CH:16]=5)=[N:21][NH:22]4)=[CH:27][CH:26]=3)[C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1Participants
Procedure
The title compound (E/Z=3:1, 63 mg, 84%) was synthesized as an orange solid according to the method described for Example A67 (oil temp 70° C., reflux 60 min) using 5-chloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (33.7 mg, 0.2 mmol) and (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbaldehyde (49.8 mg, 0.2 mmol). 1H NMR (400 MHz, DMSO-d6) E isomer: δ 13.83 (s, 1H), 10.92 (s, 1H), 8.91 (s, 1H), 8.57 (d, J=6.0 Hz, 3H), 8.37 (d, J=8.8 Hz, 1H), 7.95 (s, 1H), 7.90 (d, J=16.4 Hz, 1H), 7.75-7.70 (m, 2H), 7.57 (d, J=16.8 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H); Z isomer: δ 13.80 (s, 1H), 11.03 (s, 1H), 9.15 (s, 1H), 8.57 (d, J=6.0 Hz, 2H, buried under the doublet at 8.57), 8.34 (d, J=8.4 Hz, 1H, partially overlapping with the doublet at 8.37), 8.25 (d, J=9.2 Hz, 1H), 8.20 (s, 1H), 7.86 (d, J=14.4 Hz, 1H, partially overlapping with the doublet at 7.90), 7.75-7.70 (m, buried under the multiplet 7.75-7.70), 7.56 (d, J=16.8 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H); MS ESI 400.0 [M+H]+, calcd for [C22H14ClN5O+H]+ 400.1.
Workup
- customdescribed for Example A67 (oil temp 70° C., reflux 60 min)
Sources & evidence
- ORD record
- ord-2901a1d772114ccaaa99c1d42054203e
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765748B2
Reaction notes
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