HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(pyridin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(pyridin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 90030656 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(pyridin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine | HCID 72943767 | 24.5% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(pyridin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (120 mg, 0.19 mmol) was hydrolyzed by lithium hydroxide (36.7 mg, 0.27 mmol), in THF/Methanol/water (2/2/1 ml) to afford 22 mg 24.3% yield of pure compound after purification by preparative TLC (SiO2) using 5% methanol in chloroform as eluent. 1H NMR (DMSO-d6, 300 MHz): δ 8.44-8.3 (b, 1H), 7.899-7.877 (d, 1H), 7.767-7.743 (s, 1H), 7.44 (m, 1H), 7.34-7.30 (m, 1H), 7.02-6.99 (m, 1H), 6.87-6.84 (m, 1H), 5.32 (s, 1H), 2.16 (s, 6H). MS: 453.2 m/z=(M+1), HPLC: 93.5% in method A.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-63e164f99b75449f8807ae0b53d8b91b |
| Source note | uspto-grants-2016_05 |