Water → 5-Bromo-1-methyl-3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-pyrrolo[2,3-b]pyridine

HRID 879498Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([CH3:12])[C:5]2=[N:6][CH:7]=1.[CH3:13][N:14]1[CH2:19][CH:18]=[C:17](B(O)O)[CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.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[CH:3]=[C:4]2[C:10]([C:17]3[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH:16]=3)=[CH:9][N:8]([CH3:12])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 5-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (180 mg, 0.534 mmol) and 1-methyl-1,2,3,6-tetrahydropyridin-4-boronic acid (155 mg, 0.694 mmol) in dioxane (5.4 mL, degassed) was added tetrakis(triphenylphosphine)palladium(0) (75 mg, 0.064 mmol), K2CO3 (369 mg, 2.67 mmol) and water (1.8 mL, degassed). The reaction mixture was heated at 40° C. for 15 h, cooled and partitioned between ethyl acetate and brine. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C14H16BrN3: 306.2 (M+H+); Found: 306.2 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-607750cc09e944d38a82ea5260d842d9
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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