Potassium Carbonate → 6-(3-bromophenyl)-1-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 510321Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[N:10]([CH3:11])[N:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[Br:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:3]=[C:4]3[N:10]([CH3:11])[N:9]=[CH:8][C:5]3=[N:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 6-bromo-1-methyl-1H-pyrazolo[4,3-b]pyridine (120 mg, 0.566 mmol) and 3-bromophenylboronic acid (136 mg, 0.679 mmol) in degassed 1,4-dioxane (6 mL) and water (2 mL) was added K2CO3 (391 mg, 2.83 mmol) and tetrakis(triphenylphosphine)palladium(0) (32 mg, 0.028 mmol). The reaction mixture was heated at 90° C. for 1 h, cooled and partitioned between ethyl acetate and brine. The organic layer was separated, dried over Na2SO4 and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C13H10BrN3: 288.01 (M+H+); Found: 288.2 (M+H+).

Workup

temperaturecooled
custompartitioned between ethyl acetate and brine
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated
customto give crude which
customwas purified by chromatographic column

Sources & evidence

ORD record: ord-fcb13a1e9b554d77936514fbb6f5935a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096586B2

Reaction notes

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