Cesium carbonate → 1-(4-methoxybenzyl)-5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 715045Notes

Reaction equation

HRID 715045 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15](B4OC(C)(C)C(C)(C)O4)[CH:16]=[C:11]3[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.Br[C:29]1[CH:42]=[CH:41][C:32]([CH2:33][N:34]2[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]2)=[CH:31][CH:30]=1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.C(Cl)Cl.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>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:42]4[CH:29]=[CH:30][CH:31]=[C:32]([CH2:33][N:34]5[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]5)[CH:41]=4)[CH:16]=[C:11]3[CH:10]=[CH:9]2)=[CH:26][CH:27]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 221976121-[(4-Bromophenyl)methyl]-4-methylpiperazineHCID 683884711-(4-methoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 683884751-(4-methoxybenzyl)-5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A stirred solution of 1-(4-methoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (147PG) (50 mg, 0.137 mmol) and 1-(4-bromobenzyl)-4-methylpiperazine (121) (37 mg, 0.137 mmol, 1.1 eq) in DME (10 mL) was degassed and purged with N2 for 10 min and Cs2CO3 (2.0 eq) was added and the reaction mixture purged and degassed again. To this reaction mixture was added Pd(PPh3)4 (0.04 eq) and the resulting reaction was heated at 90° C. for 12 hrs in sealed tube condition. After completion of the reaction the contents were was cooled and diluted with CH2Cl2 and filtered through Celite bed. The CH2Cl2 layer was completely distilled off to get the crude product. The crude was passed through 100-200 mesh silica gel, eluting the pure compound 1-(4-methoxybenzyl)-5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine 151 obtained with 5% MeOH in CH2Cl2 as an off-white coloured solid in 30 mg quantity.

Workup

  1. custompurged with N2 for 10 min
  2. customthe reaction mixture purged
  3. customdegassed again
  4. customthe resulting reaction
  5. customAfter completion of the reaction the contents
  6. temperaturewere was cooled
  7. filtrationfiltered through Celite bed
  8. distillationThe CH2Cl2 layer was completely distilled off
  9. customto get the crude product
  10. washeluting the pure compound 1-(4-methoxybenzyl)-5-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridine 151
  11. customobtained with 5% MeOH in CH2Cl2 as an off-white coloured solid in 30 mg quantity

Sources & evidence

ORD record
ord-44be677384114cde8f0c5dd51f09be20
Source dataset
uspto-grants-2015_11
Patent number
US09187473B2

Reaction notes

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