Lithium Hydroxide → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 531620Notes

Reaction equation

HRID 531620 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:43]=[CH:44][CH:45]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[CH:9]=[N:8]1.[OH-].[Li+]>C1COCC1.CO.O>[F:2][C:3]1[CH:4]=[C:5]([CH:43]=[CH:44][CH:45]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 1185240853-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

Product 1

HCID 900305953-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 511.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride (170 mg, 0.026 mmol) was hydrolyzed by lithium hydroxide (12 mg, 0.264 mmol) in THF/methanol/water (10/5/2.5 ml) to yield 60 mg (40% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.54 (s, 2H), 8.229-8.227 (d, 1H), 7.959-7.957 (d, 1H), 7.73-7.70 (m, 3H), 7.44-7.41 (d, 2H), 7.38-7.23 (m, 1H), 7.12-7.09 (d, 1H), 7.08-7.00 (m, 2H), 5.43 (s, 2H), 3.55-3.50 (d, 2H), 3.21-3.13 (m, 2H), 3.05-2.93 (m, 1H), 2.16-2.11 (d, 2H), 2.02-1.89 (m, 2H). MS: m/z=452.5 (M+1), HPLC: 96.75% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-ee8c3130dfd94ea790c73524f82498aa
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…