Potassium Phosphate, Tribasic → HCID 67377267, compound

HRID 1422492Notes

Reaction equation

HRID 1422492 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][C:13]2[N:21]=[C:20](Cl)[N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][N:17]3[CH:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:2]1.[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[N:34][CH:35]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[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.O1CCOCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][C:13]2[N:21]=[C:20]([C:32]3[CH:33]=[N:34][CH:35]=[C:30]([F:29])[CH:31]=3)[N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][N:17]3[CH:23]([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:2]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 86643466HCID 86643466, compound

Product 1

HCID 67377267HCID 67377267, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A 150 ml pressure tube was charged with methyl 2-(6-(2-(1H-indol-3-yl)ethylamino)-2-chloro-9H-purin-9-yl)propanoate (c) (300 mg, 0.75 mmol), 5-fluoropyridin-3-ylboronic acid (159 mg, 1.1 mmol), tetrakis(triphenylphosphine)-palladium(0) (87 mg, 0.075 mmol), K3PO4 (638 mg, 3.0 mmol), and anhydrous dioxane (15 mL). The pressure tube was sparged with nitrogen and was sealed, then the reaction mixture was heated at 130° C. for 6 h with stirring. Water was added to the cooled mixture, and the mixture was extracted with ethyl acetate (50 ml×3). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (10 to 80% ethyl acetate in hexane eluant) to afford the title compound contaminated with a small amount of triphenylphosphine oxide. MS m/z 460.1 (M+1).

Workup

  1. customThe pressure tube was sparged with nitrogen
  2. customwas sealed
  3. additionWater was added to the cooled mixture
  4. extractionthe mixture was extracted with ethyl acetate (50 ml×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (10 to 80% ethyl acetate in hexane eluant)

Sources & evidence

ORD record
ord-b0278eb28bea4df194775ff4a4e5fc17
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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