Lithium Hydroxide → N-(4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxyacetamide

HRID 2203856Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[Cl:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=[C:10]2[NH:18][CH:19]=[C:20]([NH2:21])[C:9]=12.[Li+].[OH-]>N1C=CC=CC=1.C1COCC1>[Cl:7][C:8]1[C:13]([C:14]([F:17])([F:15])[F:16])=[CH:12][N:11]=[C:10]2[NH:18][CH:19]=[C:20]([NH:21][C:4](=[O:5])[CH2:3][O:2][CH3:1])[C:9]=12

Participants

Conditions

Temperature: 0 °C

Procedure

2-Methoxyacetyl chloride (0.074 mL, 0.76 mmol) was added to a solution of 4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-amine (120 mg, 0.51 mmol, Example 12, Steps A-G) in pyridine (5 mL) at 0° C. The reaction was stirred at 0° C. for 10 minutes, and the pyridine was removed in vacuo. The residue obtained was dissolved in THF (5 mL), treated with 2N LiOH (3 mL) and stirred for 20 minutes. THF was then removed under reduced pressure, and the aqueous slurry obtained was extracted with water (20 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with brine, dried (Na2SO4) and concentrated in vacuo to provide N-(4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxyacetamide (154 mg, 98% yield) as a solid.

Workup

customthe pyridine was removed in vacuo
customThe residue obtained
stirringstirred for 20 minutes
customTHF was then removed under reduced pressure
customthe aqueous slurry obtained
extractionwas extracted with water (20 mL) and ethyl acetate (50 mL)
customThe organic layer was separated
washwashed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3c93ea2fb2024af68ab61af7c259ee2c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365568B2

Reaction notes

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