Cesium carbonate → HCID 71090249, compound

HRID 331059Notes

Reaction equation

HRID 331059 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:22]([CH3:24])[CH3:23])[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[CH:12]=3)[C:3]=12.[CH3:25][N:26]1[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[N:27]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C1C=CC=CC=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>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]>[CH:22]([N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([NH:34][S:31]([C:28]3[CH:29]=[CH:30][N:26]([CH3:25])[N:27]=3)(=[O:33])=[O:32])=[C:3]2[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:12]=2)=[CH:9]1)([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 148356431-methyl-1H-pyrazole-3-sulfonamideHCID 710901324-bromo-1-isopropyl-3-(3-(pyrrolidin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 71090249HCID 71090249, compoundYield 67.6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

A mixture of 4-bromo-1-isopropyl-3-(3-(pyrrolidin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine (D15) (400 mg, 1.041 mmol), 1-methyl-1H-pyrazole-3-sulfonamide (D94) (252 mg, 1.561 mmol), cesium carbonate (678 mg, 2.082 mmol), Pd2(dba)3 (71.5 mg, 0.078 mmol) and 2-(dimethylamino)-2′-(dicyclohexylphosphino)biphenyl (61.4 mg, 0.156 mmol) in 1,4-dioxane (4.5 mL) was heated under an atmosphere of nitrogen in a microwave at 150° C. for 30 minutes. The mixture was then filtered through celite, washing with ethyl acetate, and evaporated to dryness. The residues were purified on silica eluting with cyclohexane and ethyl acetate (0-100%). The appropriate fractions were combined and evaporated to dryness producing an impure material (327 mg). This was purified via MDAP (acidic) twice. The appropriate fractions were combined and evaporated to dryness to give the title compounds (131 mg). LCMS (A): m/z (M+H)+ 465, C24H28N6O2S requires 464 (acidic).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with ethyl acetate
  3. customevaporated to dryness
  4. customThe residues were purified on silica eluting with cyclohexane and ethyl acetate (0-100%)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-877fa217b58c4842bfbdcb9467c41e46
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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