Nitrogen → 3-Bromo-6-methylpyridine-2-carboxylic acid

HRID 517676Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:9]([O:11]C)=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)C1OC=CN=1)CCC.N#N>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In a microwave vial was dissolved the title compound of step B (185 mg, 0.8 mmol) and 2-(tributylstannyl)oxazole (0.22 mL, 1 mmol) in PhCH3 (2.4 mL). The solution was degassed with N2 and Pd(PPh3)4 (92 mg, 0.1 mmol) were added. The reaction was purged with N2 and heated at 120° C. for 20 m using microwave irradiation. The reaction was cooled to rt, filtered through a pad of celite and purified via silica gel chromatography (0-40% EtOAc in hexanes) to give the title compound of step A (333 mg, 67%). The mixture was diluted with H2O and extracted with EtOAc. The combined organics were dried (MgSO4) and purified via silica gel chromatography (0-50% EtOAc in heptane) to give the title compound (56 mg, 32%). MS (ESI) mass calcd. for C11H10N2O3, 218.2; m/z found 219.1 [M+H]+.

Workup

additionwere added
customThe reaction was purged with N2
custommicrowave irradiation
temperatureThe reaction was cooled to rt
filtrationfiltered through a pad of celite
custompurified via silica gel chromatography (0-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-0879a7457bfb47f9a4f9287d6c8aedbd
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115117B2

Reaction notes

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