Nitrogen → 4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1821310Notes

Reaction equation

HRID 1821310 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:3]=12.[CH3:24][N:25]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[C:27]([C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=2)=[N:26]1.N#N>O1CCOCC1.C([O-])(O)=O.[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:24][N:25]1[CH:29]=[C:28]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([S:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)(=[O:17])=[O:16])[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:3]=23)[C:27]([C:39]2[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=2)=[N:26]1

Participants

7

Reactant 3

HCID 947NitrogenHCID 687417291-methyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 689992204-bromo-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 689972904-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridineYield 36%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 4-bromo-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine (37 mmol) and 1-methyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (37 mmol) in 1,4-dioxane (300 ml) and saturated NaHCO3(aq) (100 ml) was degassed with N2 for 10 minutes after which time tetrakis(triphenylphosphine) palladium(0) (1.85 mmol) was added and the resulting mixture was heated at 105° C. overnight. The reaction was then concentrated, diluted with CHCl3 (200 ml) and EtOAc (200 ml), sonicated for 10 minutes, filtered through Celite 545, and concentrated to yield a red oil which was purified on 400 g silica gel (CHCl3/EtOAc w/0.1% MeOH) to give the title product as a light yellow foam (36%). ESMS [M+H]+: 532.0.

Workup

  1. additionwas added
  2. concentrationThe reaction was then concentrated
  3. additiondiluted with CHCl3 (200 ml) and EtOAc (200 ml)
  4. customsonicated for 10 minutes
  5. filtrationfiltered through Celite 545
  6. concentrationconcentrated
  7. customto yield a red oil which
  8. customwas purified on 400 g silica gel (CHCl3/EtOAc w/0.1% MeOH)

Sources & evidence

ORD record
ord-b15512d8e234444ca452dbab385107dd
Source dataset
uspto-grants-2009_10
Patent number
US07605266B2

Reaction notes

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