Potassium Carbonate → isopropyl 4-(1H-pyrrolo[3,2-b]pyridin-6-yl)picolinate

HRID 2178595Notes

Reaction equation

[CH:1]([O:4][C:5](=[O:13])[C:6]1[CH:11]=[C:10](Cl)[CH:9]=[CH:8][N:7]=1)([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:22]2[CH:23]=[C:24]3[NH:30][CH:29]=[CH:28][C:25]3=[N:26][CH:27]=2)O1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[NH:30]1[C:24]2[C:25](=[N:26][CH:27]=[C:22]([C:10]3[CH:9]=[CH:8][N:7]=[C:6]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:13])[CH:11]=3)[CH:23]=2)[CH:28]=[CH:29]1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 4-chloropicolinic acid isopropyl ester (1.5 g, 7.5 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[3,2-b]pyridine (1.83 g, 7.5 mmol), dppf(Pd)Cl2 (270 mg, 5 mol %), and potassium carbonate (2.0 g, 15 mmol) in degassed toluene (8 mL), degassed water (4 mL) and degassed isopropanol (4 mL) was heated at 65° C. for 2 hours. The aqueous phase was discarded and the solvent removed under reduced pressure. The residue was purified by flash chromatography (rf: 0.41 in 20:1 ethyl acetate:methanol) to provide isopropyl 4-(1H-pyrrolo[3,2-b]pyridin-6-yl)picolinate (1.20 g, 57%) as a yellow powder. 282.1 (M+1).

Workup

customdegassed water (4 mL)
customdegassed isopropanol (4 mL)
customthe solvent removed under reduced pressure
customThe residue was purified by flash chromatography (rf: 0.41 in 20:1 ethyl acetate:methanol)

Sources & evidence

ORD record: ord-68900d9cca5848109ada00e2f8c49b6f
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067933B2

Reaction notes

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