3-Nitrophenylboronic Acid → HCID 123358842, compound

HRID 882157Notes

Reaction equation

HRID 882157 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:4]=2[N:5]=[CH:6][N:7]=1.[N+:19]([C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.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]>[N+:19]([C:22]1[CH:27]=[C:26]([C:2]2[C:3]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:4]=3[N:5]=[CH:6][N:7]=2)[CH:25]=[CH:24][CH:23]=1)([O-:21])=[O:20]

Participants

7

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 467367974-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 123358842HCID 123358842, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (15.0 g, 52.9 mmol) in N,N-dimethylformamide (200 mL) was added to Pd(dppf)Cl2 (2.2 g, 2.7 mmol), (3-nitrophenyl)boronic acid (13.3 g, 79.7 mmol) under nitrogen. A solution of sodium carbonate (6.00 g, 56.6 mmol) in water (60.0 mL) was then added and the reaction was stirred for 3 hours at 100° C. The resulting mixture was concentrated in vacuo, and the solids were filtered and extracted with dichloromethane (×3). The combined organic layers were washed with H2O, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The reaction was then purified by chromatography using silica gel, eluting with 0-33% EtOAc/petroleum ether. The product was collected and concentrated in vacuo to afford 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine as a yellow solid. LRMS (ESI) calc'd for C18H23N4O3Si [M+H]+: 371, found 371.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. filtrationthe solids were filtered
  3. extractionextracted with dichloromethane (×3)
  4. washThe combined organic layers were washed with H2O, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe reaction was then purified by chromatography
  9. washeluting with 0-33% EtOAc/petroleum ether
  10. customThe product was collected
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84ffd8bfe6bf4eaf90d0a3526a62a22c
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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