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

HRID 879498
Notes
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Reaction equation

HRID 879498 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 53407231(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)boronic acidHCID 598120775-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 867003155-Bromo-1-methyl-3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

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

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and brine
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude which
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes