Cyclopentanecarbonyl chloride → N-(5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopentanecarboxamide

HRID 1923945Notes

Reaction equation

C(N(C(C)C)C(C)C)C.[CH:10]1([C:15](Cl)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1.[Cl:18][C:19]1[C:20]([F:29])=[C:21]2[C:27]([NH2:28])=[CH:26][NH:25][C:22]2=[N:23][CH:24]=1>C1COCC1>[Cl:18][C:19]1[C:20]([F:29])=[C:21]2[C:27]([NH:28][C:15]([CH:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[O:16])=[CH:26][NH:25][C:22]2=[N:23][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-Ethyl-N-isopropylpropan-2-amine (279 mg, 2.16 mmol) followed by cyclopentanecarbonyl chloride (143 mg, 1.08 mmol) were added dropwise to 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 1.08 mmol) in THF (10 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and then concentrated to dryness. The residue was triturated in water and then filtered. The solid was washed with ACN and dried under vacuum to provide N-(5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopentanecarboxamide (186 mg, 61% yield) as a solid.

Workup

concentrationconcentrated to dryness
customThe residue was triturated in water
filtrationfiltered
washThe solid was washed with ACN
customdried under vacuum

Sources & evidence

ORD record: ord-50fce399e98d417a8ea8fff41f9d9d56
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178131B2

Reaction notes

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