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Cesium carbonate → N-(1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-methyl-1H-pyrazole-3-sulfonamide

HRID 331062
Notes
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Reaction equation

HRID 331062 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:22])[C:9]([CH3:21])=[C:10]([C:11]3[CH:19]=[C:18]4[C:14]([CH2:15][CH2:16][N:17]4[CH3:20])=[CH:13][CH:12]=3)[C:3]=12.[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[N:25]1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:22][N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([NH:32][S:29]([C:26]3[CH:27]=[CH:28][N:24]([CH3:23])[N:25]=3)(=[O:31])=[O:30])=[C:3]2[C:10]([C:11]2[CH:19]=[C:18]3[C:14]([CH2:15][CH2:16][N:17]3[CH3:20])=[CH:13][CH:12]=2)=[C:9]1[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 148356431-methyl-1H-pyrazole-3-sulfonamideHCID 710901424-bromo-1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 71090219
N-(1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-methyl-1H-pyrazole-3-sulfonamide
Yield 32.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-bromo-1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridine (D28) (390 mg, 1.095 mmol), 1-methyl-1H-pyrazole-3-sulfonamide (D94) (265 mg, 1.642 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (95 mg, 0.164 mmol), cesium carbonate (1070 mg, 3.28 mmol) and Pd2(dba)3 (75 mg, 0.082 mmol) in 1,4-dioxane (10 mL) was refluxed for 7 hours. After cooled to RT, the reaction mixture was filtered through celite, washing with DCM and the resulting solution was evaporated to dryness. DCM was added to the residue and the resulting solid was filtered and then taken up in formic acid/DMSO (1:1), purified by MDAP (acidic condition) to give the title compound (155 mg). LCMS (A): m/z (M+H)+ 437, C22H24N6O2S requires 436 (acidic).

Workup

  1. temperaturewas refluxed for 7 hours
  2. filtrationthe reaction mixture was filtered through celite
  3. washwashing with DCM
  4. customthe resulting solution was evaporated to dryness
  5. additionDCM was added to the residue
  6. filtrationthe resulting solid was filtered
  7. custompurified by MDAP (acidic condition)

Sources & evidence

ORD record
ord-c5c02f3ca8a145d5b77f79e12ed09d71
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877742B2

Reaction notes

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