Sodium Carbonate → HCID 58827137, compound

HRID 1877960Notes

Reaction equation

HRID 1877960 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[CH:14]=[N:15][CH:16]=[C:12]2[CH:11]([CH3:17])[CH2:10][CH2:9]1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[CH:14]=[N:15][CH:16]=[C:12]2[CH:11]([CH3:17])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58827169HCID 58827169, compound

Product 1

HCID 58827137HCID 58827137, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5-(2-bromophenyl)-8-methyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine (573 mg, 1.97 mmol) in DME (10 mL) is added phenylboronic acid (480 mg, 3.94 mmol), aqueous Na2CO3 (2M, 4 mL, 8.0 mmol), and Pd(PPh3)4 (500 mg). The reaction mixture is stirred at reflux overnight. The mixture is partitioned between EtOAc and brine. The organic layer is washed by brine, dried over Na2SO4 and concentrated to give an oil, which is subjected to flash chromatography (silica gel) eluting with MeOH:CH2Cl2 to yield the desired compound. MS (ESI) m/z 289 (M+H)

Workup

  1. temperatureat reflux overnight
  2. customThe mixture is partitioned between EtOAc and brine
  3. washThe organic layer is washed by brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give an oil, which
  7. washeluting with MeOH

Sources & evidence

ORD record
ord-b669aed9afd54d95a0ab66f08861be89
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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