Isoquinoline-4-boronic acid → 4-((2-Phenylpyrimidin-5-yl)methyl)isoquinoline

HRID 1054117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054117
Br[CH2:2][C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](B(O)O)=[CH:17][N:16]=1>>[C:9]1([C:6]2[N:5]=[CH:4][C:3]([CH2:2][C:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:15]=[N:16][CH:17]=3)=[CH:8][N:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

3

Edukt 2

HCID 3761204Isoquinoline-4-boronic acidHCID 218300465-(Bromomethyl)-2-phenylpyrimidine

Produkt 1

HCID 573300834-((2-Phenylpyrimidin-5-yl)methyl)isoquinoline

Versuchsvorschrift

Synthesized using compound 64a (85 mg, 0.34 mmol) and isoquinolin-4-ylboronic acid (104 mg, 0.60 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (3:1) as eluent. After flash chromatography the product was solved in ethyl acetate and a few drops of conc. HCl and water were added. After stirring for 30 minutes the phases were separated and water phase was neutralized with aqueous Na2CO3-solution (2M). After extraction with ethyl acetate and drying over MgSO4 the solvent was removed under vacuum. Orange solid. Yield: 68 mg, 67%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=4.40 (s, 2H), 7.44-7.51 (m, 3H), 7.61-7.67 (m, 1H), 7.67-7.74 (m, 1H), 7.87 (dd, J=8.4, 0.8 Hz, 1H), 8.02-8.06 (m, 1H), 8.37-8.42 (m, 2H), 8.49 (s, 1H), 8.66 (s, 2H), 9.24 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=30.9, 122.8, 127.4, 127.5, 127.9, 128.6, 128.6, 128.6, 130.4, 130.6, 131.0, 134.3, 137.2, 143.6, 152.7, 157.0, 163.1; (ESI): m/z=297.91 [M+H]+.

Aufarbeitung

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (3:1) as eluent
  4. additiona few drops of conc. HCl and water were added
  5. customwere separated
  6. extractionAfter extraction with ethyl acetate
  7. dry with materialdrying over MgSO4 the solvent
  8. customwas removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-310553eb9bf34773ba0153084c9b6891
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394290B2

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