Bromide ion → 6-[5-(3-Hydroxypropyl)imidazol-1-ylmethyl]biphenyl-3-carbonitrile

HRID 1877961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877961
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][N:11]1[C:15]([CH2:16][CH2:17][CH2:18][OH:19])=[CH:14][N:13]=[CH:12]1)[C:5]#[N:6].N1C=CN=C1.[Br-].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[OH:19][CH2:18][CH2:17][CH2:16][C:15]1[N:11]([CH2:10][C:9]2[C:2]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:3][C:4]([C:5]#[N:6])=[CH:7][CH:8]=2)[CH:12]=[N:13][CH:14]=1

Komponenten

7

Edukt 5

HCID 259Bromide ionHCID 795ImidazoleHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 668861184-{5-[3-Hydroxypropyl]imidazol-1-ylmethyl}-3-bromobenzonitrile

Produkt 1

HCID 588272366-[5-(3-Hydroxypropyl)imidazol-1-ylmethyl]biphenyl-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15220664Palladium--triphenylphosphane (1/1)Katalysator

Versuchsvorschrift

To a solution of 3-bromo-4-[5-(3-hydroxypropyl)-imidazol-1-ylmethyl]benzonitrile (1.02 g, 3.2 mmol) that is prepared by alkylation of imidazole from Example 21 with bromide described in Example 1C followed by removal of the silyl protecting group by analogy to the first step in Example 3C in DME (10 mL) is added phenylboronic acid (586 mg, 4.8 mmol), aqueous Na2CO3 (2M, 4.8 mL, 9.6 mmol), and PS—PPh3-Pd (O) resin (0.13 mmol/g, 1 g). The reaction mixture is run in a microwave at 130° C. for 20 min. The mixture is partitioned between EtOAc and brine. The organic layer is washed with brine, dried over Na2SO4 and concentrated to give oil.

Aufarbeitung

  1. customfollowed by removal of the silyl protecting group by analogy to the first step in Example 3C in DME (10 mL)
  2. customThe mixture is partitioned between EtOAc and brine
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give oil

Quellen und Nachweise

ORD-Eintrag
ord-b06f812c44e34e0ab02380b47537d47b
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314097B2

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