HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 118524053 | — |
| Reactant | 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride | HCID 118524085 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine | HCID 72944752 | 86.6% |
Reaction Steps
Using similar reaction conditions as described in step-iii of example-1, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (60 mg, 0.087 mmol) was hydrolyzed with lithium hydroxide (19 mg, 0.438 mmol) in THF/methanol/water (5/1/1 mL) to yield 40 mg (70.17% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.63-8.62 (d, 1H), 8.54 (s, 1H), 8.29 (s, 1H), 7.99 (s, 1H), 7.77 (s, 1H), 7.69-7.67 (d, 2H), 7.40-7.38 (q, 1H), 7.18-7.02 (m, 5H), 5.46 (s, 2H), 3.40-3.37 (m, 8H), 2.91 (s, 3H). MS: m/z=531.0 (M+1), HPLC: 99.35% in method B.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-598d67659ebd423582f403e751e338f4 |
| Source note | uspto-grants-2016_05 |