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

HRID 531563Notes

Reaction equation

HRID 531563 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=5)=[CH:23][CH:22]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[C:8]([CH3:43])=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([C:27]5[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:43])=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 900306563-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(pyridin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 729437673-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(pyridin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 24.5%

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)-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.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-63e164f99b75449f8807ae0b53d8b91b
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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