Ethanol → HCID 21081639, compound

HRID 2117152Notes

Reaction equation

HRID 2117152 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.CCOC(C)=O>[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

7

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 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

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 h with vigorous stirring. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The mixture was washed with saturated aq. NaHCO3 solution and brine, dried (MgSO4), and concentrated 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. customThe tube was sealed
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. washThe mixture was washed with saturated aq. NaHCO3 solution and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (SiO2, eluting with 2% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-d9afa50265434ed9a95ca1240a4166ef
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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