Water → HCID 68283796, compound

HRID 1527255Notes

Reaction equation

HRID 1527255 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:12]2[N:13]=[CH:14][N:15]=[CH:16][C:11]=2[C:10](Br)=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:24]([O:26]CC)=[CH2:25])CCC.O>C1(C)C=CC=CC=1.[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>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:12]2[N:13]=[CH:14][N:15]=[CH:16][C:11]=2[C:10]([C:24](=[O:26])[CH3:25])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 68283893HCID 68283893, compound

Product 1

HCID 68283796HCID 68283796, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of (5-bromo-pyrrolo[2,3-d]pyrimidin-7-yl)-acetic acid tert-butyl ester (220 mg, 0.71 mmol), tri-butyl(1-ethoxyvinyl)tin (285 μL, 0.85 mmol) and tetrakis(triphenylphosphine) palladium (16.28 mg, 14.1 μmol) in toluene (7 mL) was heated at 110° C. for 72 h under argon atmosphere. The mixture was allowed to cool to RT, poured into water and extracted with EtOAc (×2). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (CH2Cl2 to CH2Cl2/MeOH 94:6). TLC, Rf (CH2Cl2/MeOH 9:1)=0.54; MS (UPLC/MS): 276.3 [M+H]+, 320.4 [M+HCOO]−; tR (HPLC conditions f): 1.40 min.

Workup

  1. extractionextracted with EtOAc (×2)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash column chromatography on silica gel (CH2Cl2 to CH2Cl2/MeOH 94:6)
  6. custom1.40 min.

Sources & evidence

ORD record
ord-c81530af0e2f4f28bb9b960aa7e625f1
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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