Bromide ion → HCID 70925729, compound

HRID 923280Notes

Reaction equation

HRID 923280 reaction equation
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#N.[NH:20]1[CH:24]=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][CH:4]=[C:7]([C:24]#[N:20])[CH:8]=2)[CH:12]=[N:13][CH:14]=1

Participants

7

Reactant 5

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

Product 1

HCID 70925729HCID 70925729, compound

Reagents, catalysts & solvents 1

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

Procedure

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 (0) 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.

Workup

  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

Sources & evidence

ORD record
ord-e97a9f1d23d441fd969708f444c6e1cb
Source dataset
uspto-grants-2016_03
Patent number
US09278969B2

Reaction notes

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