Sodium Carbonate → 5-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine

HRID 880013Notes

Reaction equation

HRID 880013 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:11][N:12]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[N:13]1.C(=O)([O-])[O-].[Na+].[Na+]>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.CN(C=O)C>[CH3:11][N:12]1[CH:16]=[C:15]([C:2]2[CH:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH:14]=[N:13]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 580861115-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridineYield 90.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

25 g of 5-bromo-1H-pyrrolo[2,3-b]pyridine 1 and 40 g of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole are dissolved 350 ml of DMF, and 20 g of tetrakis(triphenylphosphine)palladium are added under protective gas. After addition of 190 ml of 2N sodium carbonate solution, the batch is stirred at 100° C. for 12 h. All volatile constituents are removed in vacuo, and the residue is partitioned between ethyl acetate and water. Insoluble constituents are filtered off. After extraction of the aqueous phase, the combined organic phases are dried over sodium sulfate, filtered and evaporated to ¼ of the volume in vacuo. The crystal batch formed after 12 h at 0° C. is filtered off and combined with the first solid fraction, giving 22.7 g of compound 2; HPLC-MS: Rt=1.400 min; [M+H+]: 199.1.

Workup

  1. additionare added under protective gas
  2. customAll volatile constituents are removed in vacuo
  3. customthe residue is partitioned between ethyl acetate and water
  4. filtrationInsoluble constituents are filtered off
  5. extractionAfter extraction of the aqueous phase
  6. dry with materialthe combined organic phases are dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crystal batch formed after 12 h at 0° C.
  10. filtrationis filtered off

Sources & evidence

ORD record
ord-9978f4f6acb94869b65f7172774bf1b7
Source dataset
uspto-grants-2015_03
Patent number
US08993564B2

Reaction notes

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