Ethanol → HCID 21081639, compound

HRID 347548Notes

Reaction equation

HRID 347548 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[F:21])[N:4]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:3]=1.[N:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(O)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1>[F:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[N:4]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:3]=[C:2]([C:33]3[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=3)[C:10]=12

Participants

6

Reactant 4

HCID 702EthanolHCID 62657Potassium Phosphate, TribasicHCID 2734379(Pyridin-4-yl)boronic acidHCID 21081597HCID 21081597, compound

Product 1

HCID 21081639HCID 21081639, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A sealed tube was charged with a solution of 3-bromo-4-(2-fluoro-4-nitrophenoxy)-1-((2-(trimethylsilyl) ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (480 mg, 1.0 mmol) in toluene (5 mL), pyridin-4-ylboronic acid (246 mg, 2.0 mmol, Lancaster), 0.5 mL of ethanol, and potassium phosphate (1.0 mL, 2 M solution, 2.0 mmol). Argon was bubbled through the mixture for 15 minutes, and the reaction mixture was treated with tetrakis(triphenylphosphine)Pd(0)(58) mg, 0.05 mmol, Strem). the tube was sealed and the mixture was heated at 95 ° C. for 18 with vigorous stirring. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The mixture ws washed with sasturated aq. NaHCO3 solution and brine, dried (MgSO4), and concentated in vacuo. The residue was purified by flash chromatography (SiO2, eluting with 2% MeOH in dichloromethane) to give the desired product (237 mg, 49%) as a thick brown oil. MS(ESI+) m/z 481.1 (M+H)+.

Workup

  1. customArgon was bubbled through the mixture for 15 minutes
  2. additionthe reaction mixture was treated with tetrakis(triphenylphosphine)Pd(0)(58) mg
  3. customthe tube was sealed
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. additiondiluted with EtOAc
  6. washThe mixture ws washed with sasturated aq. NaHCO3 solution and brine
  7. dry with materialdried (MgSO4)
  8. customThe residue was purified by flash chromatography (SiO2, eluting with 2% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-d78c556669c94af79eab434c4c7c68f8
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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