Potassium Carbonate → HCID 86706946, compound

HRID 1750264Notes

Reaction equation

HRID 1750264 reaction equation
[Cl:1][C:2]1[C:3]2[C:10](I)=[C:9]([CH3:12])[N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]=2[N:5]=[CH:6][N:7]=1.[C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)#[N:22].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[C:3]2[C:10]([C:27]3[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=3)[C:21]#[N:22])=[C:9]([CH3:12])[N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 86706945HCID 86706945, compound

Product 1

HCID 86706946HCID 86706946, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-chloro-5-iodo-6-methyl-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (C6) (300 mg, 0.71 mmol) and (3-cyanophenyl)boronic acid (104 mg, 0.708 mmol) in a mixture of 1,2-dimethoxyethane and water (5:1, 10 mL) was added potassium carbonate (193 mg, 1.40 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (17 mg, 23 μmol). The reaction mixture was degassed and purged with nitrogen; this procedure was carried out a total of three times. After heating at reflux for 18 hours, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in petroleum ether) afforded the product as a yellow oil. Yield: 140 mg, 0.351 mmol, 50%. LCMS m/z 399.2 [M+H+].

Workup

  1. customThe reaction mixture was degassed
  2. custompurged with nitrogen
  3. temperatureAfter heating
  4. temperatureat reflux for 18 hours
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-ccd67604223d4531a646d31970d7c231
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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