Sodium Carbonate → HCID 59578408, compound

HRID 1897797Notes

Reaction equation

HRID 1897797 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-8be649a03e9d4b34a54c09e51fcebaa7
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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