Sodium Carbonate → HCID 59578408, compound

HRID 391313Notes

Reaction equation

HRID 391313 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([CH:6]=[C:7](B(O)O)[N:8]2[CH3:11])=[CH:4][CH:3]=1.Br[C:16]1[C:21]([CH:22]=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1.C([O-])([O-])=O.[Na+].[Na+]>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>[Cl:1][C:2]1[N:10]=[C:9]2[N:8]([CH3:11])[C:7]([C:19]3[CH:20]=[C:21]([CH:22]=[O:23])[CH:16]=[N:17][CH:18]=3)=[CH:6][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 47149512-BromonicotinaldehydeHCID 59578424HCID 59578424, compound

Product 1

HCID 59578408HCID 59578408, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To 6-chloro-N-methyl-7-aza indole-2-boronic acid (1.00 g, 4.75 mmol) in dioxane (40 mL) under N2 was added 5 bromo-3-pyridine carbaldehyde (0.589 g, 3.17 mmol), aqueous Na2CO3 (2M, 4.75 mL, 9.50 mmol) and polymer bound Pd(PPh3)4 (1.760 g, 0.158 mmol). The reaction was stirred for 2 hours at 85° C. The reaction mixture was cooled to room temperature. The solids were filtered off and the precipitate was washed thoroughly with methanol. The filtrate was concentrated in vacuo to give a brown color oil. The crude was purified by silica gel flash chromatography using DCM-MeOH (90-10, v/v) to afford pure product 5-(6-Chloro-1-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-pyridine-3-carbaldehyde as a solid. ESI-MS: m/z 272.1 (M+H)+

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solids were filtered off
  3. washthe precipitate was washed thoroughly with methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a brown color oil
  6. customThe crude was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-fe8552dab6334e20a375b7f03f63cbc8
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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