Potassium Carbonate → 1-(4-{4-[3-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzyl}-piperazin-yl)-ethanone

HRID 85049Notes

Reaction equation

HRID 85049 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][CH:4]=1.[C:18]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:20])[CH3:19].C([O-])([O-])=O.[K+].[K+].Br[C:34]1[CH:35]=[C:36]2[C:42]([C:43]3[CH:44]=[C:45]4[C:49](=[CH:50][CH:51]=3)[NH:48][CH:47]=[CH:46]4)=[CH:41][N:40](S(C3C=CC(C)=CC=3)(=O)=O)[C:37]2=[N:38][CH:39]=1>CN(C=O)C.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>[NH:48]1[C:49]2[C:45](=[CH:44][C:43]([C:42]3[C:36]4[C:37](=[N:38][CH:39]=[C:34]([C:6]5[CH:5]=[CH:4][C:3]([CH2:2][N:24]6[CH2:25][CH2:26][N:21]([C:18](=[O:20])[CH3:19])[CH2:22][CH2:23]6)=[CH:8][CH:7]=5)[CH:35]=4)[NH:40][CH:41]=3)=[CH:51][CH:50]=2)[CH:46]=[CH:47]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 837951-AcetylpiperazineHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 667791765-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 462360471-(4-{4-[3-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzyl}-piperazin-yl)-ethanoneYield 46%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (100 mg, 0.337 mmol), N-acetylpiperazine (47 mg, 0.37 mmol) and K2CO3 (93 mg, 0.675 mmol) were combined in DMF (2.5 ml) and stirred overnight at room temperature. The reaction was quenched by the addition of water, extracted with DCM and dried. The residue was taken up in CH3CN (2 ml), Intermediate B (120 mg, 0.275 mmol) and dichlorobis(triphenylphosphine)palladium (II) (10 mg, 0.013 mmol) were added and the reaction was heated to 150° C. in a microwave reactor for 20 min. The mixture was partitioned between water and DCM, the organic phase dried, evaporated and purified by silica gel chromatography using 0-5% MeOH:DCM. 53 mg (46%) of the title compound were obtained. MS ESI (m/z): 450.4 (M+1)+, calc. 449.

Workup

  1. customThe reaction was quenched by the addition of water
  2. extractionextracted with DCM
  3. customdried
  4. temperaturethe reaction was heated to 150° C. in a microwave reactor for 20 min
  5. customThe mixture was partitioned between water and DCM
  6. customthe organic phase dried
  7. customevaporated
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-89b44f887961403bb9b41854013c0a0f
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

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