Isopropyl iodide → 4-(1-isopropyl-1H-pyrrolo[3,2-b]pyridin-6-yl)picolinic acid

HRID 1909460Notes

Reaction equation

[H-].[Na+].[NH:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([C:18]([O:20]C(C)C)=[O:19])[CH:13]=3)[CH:10]=2)[CH:5]=[CH:4]1.[CH:24](I)([CH3:26])[CH3:25]>CN(C)C=O>[CH:24]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=3)[CH:10]=2)[CH:5]=[CH:4]1)([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium hydride (55 mg, 60% in mineral oil, 1.4 mmol) was added to a solution of isopropyl 4-(1H-pyrrolo[3,2-b]pyridin-6-yl)picolinate (250 mg, 0.89 mmol) in N,N-dimethylformamide (3 mL). After stirring for 10 minutes, isopropyl iodide was added and the reaction was stirred for 3 hours at room temperature. Solvent was removed from the reaction mixture under reduced pressure, and the residue dissolved in 2M HCl (3 mL) and heated at 100° C. overnight. The crude reaction mixture was purified by reverse-phase HPLC to give 4-(1-isopropyl-1H-pyrrolo[3,2-b]pyridin-6-yl)picolinic acid (50 mg, 20%). 282.1 (M+1).

Workup

stirringthe reaction was stirred for 3 hours at room temperature
customSolvent was removed from the reaction mixture under reduced pressure
dissolutionthe residue dissolved in 2M HCl (3 mL)
customThe crude reaction mixture
customwas purified by reverse-phase HPLC

Sources & evidence

ORD record: ord-edb5efb91f244c259a3750f3f19cfef7
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598360B2

Reaction notes

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