Water → 4-{3-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-benzamide

HRID 712574Notes

Reaction equation

HRID 712574 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)=[CH:13][CH:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.NC(OB([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)O)=O.[C:47]([O-:50])([O-])=O.[Na+].[Na+].O.CC#[N:56]>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>[CH3:24][N:21]1[CH2:22][CH2:23][N:18]([CH2:17][C:14]2[CH:15]=[CH:16][C:11]([C:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([C:41]5[CH:42]=[CH:43][C:44]([C:47]([NH2:56])=[O:50])=[CH:45][CH:46]=5)[CH:3]=4)[NH:8][CH:9]=3)=[CH:12][CH:13]=2)[CH2:19][CH2:20]1

Participants

7

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 66589089Aminocarbonylphenylboronic acidHCID 667788435-bromo-3-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 667799064-{3-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-benzamideYield 11%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

5-Bromo-3-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (Intermediate CD, 70 mg, 0.13 mmol), aminocarbonylphenylboronic acid (26 mg, 0.156 mmol) and dichlorobis(triphenylphosphine)palladium (II) (5 mg, 0.0065 mmol) were combined in CH3CN (2 ml) and 1 M Na2CO3 (2 ml) and reacted in a microwave reactor for 20 min at 150° C. Water was added and the aqueous phase was extracted with DCM, dried and evaporated. Purification by reversed phase chromatography using 0-100% MeOH:water yielded 6 mg (11%) of the title compound. MS ESI (m/z): 426.7 (M+1)+, calc. 425.

Workup

  1. extractionthe aqueous phase was extracted with DCM
  2. customdried
  3. customevaporated
  4. customPurification by reversed phase chromatography

Sources & evidence

ORD record
ord-511a8675343a4df994d0e1653eaec965
Source dataset
uspto-grants-2015_11
Patent number
US09181247B2

Reaction notes

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