Lithium Hydroxide → 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

HRID 2089029Notes

Reaction equation

HRID 2089029 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[C:15]([Cl:17])[N:14]=[C:13]([NH:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[CH:12]=3)=[CH:9][N:8](S(C3C=CC=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[OH-].[Li+]>O1CCCC1.CO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[C:15]([Cl:17])[N:14]=[C:13]([NH:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[CH:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 866498714-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

Product 1

HCID 871917044-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amineYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of Example 171a (0.100 g, 0.16 mmol) in 9 mL tetrahydrofuran/methanol (2:1) was treated with 1N lithium hydroxide (0.024 g, 1.00 mmol) in 1 mL water at room temperature for 16 hours. The material was diluted with water and resulting precipitate collected by filtration. Trituration with dimethyl sulfoxide/methanol and filtration afforded 54 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 1.11-1.44 (m, 5H) 1.54-1.66 (m, 1H) 1.67-1.80 (m, 2H) 1.87-1.99 (m, 2H) 3.62-3.77 (m, 1H) 6.78 (d, J=7.93 Hz, 1H) 6.86 (d, J=4.36 Hz, 2H) 8.23 (s, 1H) 8.37 (s, 1H) 8.49 (s, 1H) 12.41 (s, 1H). MS (ESI−) m/z 405.1 (M−H)−.

Workup

  1. customresulting precipitate
  2. filtrationcollected by filtration
  3. filtrationTrituration with dimethyl sulfoxide/methanol and filtration

Sources & evidence

ORD record
ord-a3e385c6ede34839968283e0abb81173
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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