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Potassium Carbonate → 1(2H)-Pyridinecarboxylic acid,4-(5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3,6-dihydro-,1,1-dimethylethyl ester

HRID 2375944
Notes
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Reaction equation

HRID 2375944 reaction equation
[Br:1][C:2]1[C:3]([Cl:12])=[C:4]2[CH:10]=[C:9](I)[NH:8][C:5]2=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]([O:23][C:24]([N:26]1[CH2:27][CH:28]=[C:29]([C:9]2[NH:8][C:5]3=[N:6][CH:7]=[C:2]([Br:1])[C:3]([Cl:12])=[C:4]3[CH:10]=2)[CH2:30][CH2:31]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 598545525-Bromo-4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 598545621(2H)-Pyridinecarboxylic acid,4-(5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridin-2-yl)-3,6-dihydro-,1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 178418476
HCID 178418476, compound
Catalyst

Procedure

To a mixture of 5-bromo-4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine (46 mg, 0.12 mmol), potassium carbonate (36 mg, 0.25 mmol), dichlorobis-(triphenylphosphine)palladium (9 mg, 0.01 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (42 mg, 0.13 mmol) were added degassed dioxane (4 mL) and water (1 mL), and the mixture was heated to reflux for 5 h. The reaction was evaporated under reduced pressure and the residue was dissolved in DCM and filtered. The DCM filtrate was evaporated and the crude product obtained was purified by chromatography on silica gel [Jones Flashmaster, 20 g/70 mL cartridge, eluting with DCM:methanol 100:0→99.5:0.5], yielding the title compound. MS (ES+): m/z 413.84 (100) [MH+]; HPLC: tR=6.95 min (ZQ2000, nonpolar—15 min).

Workup

  1. additionwere added
  2. customdegassed dioxane (4 mL) and water (1 mL)
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 5 h
  5. customThe reaction was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in DCM
  7. filtrationfiltered
  8. customThe DCM filtrate was evaporated
  9. customthe crude product obtained
  10. customwas purified by chromatography on silica gel [Jones Flashmaster, 20 g/70 mL cartridge, eluting with DCM:methanol 100:0→99.5:0.5]

Sources & evidence

ORD record
ord-e3164ee2d11f4fb2a0ddf60516f11115
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07465726B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes