Sodium Carbonate → HCID 67990225, compound

HRID 1184792Notes

Reaction equation

HRID 1184792 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19](Br)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[C:23]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)#[N:24].C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:29]4[CH:28]=[CH:27][CH:26]=[C:25]([C:23]#[N:24])[CH:30]=4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 679732624-(5-Bromo-2,3-dihydro-benzofuran-2-yl)-piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 67990225HCID 67990225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-(5-bromo-2,3-dihydro-benzofuran-2-yl)-piperidine-1-carboxylic acid isopropyl ester (37 mg) and 3-cyanophenylboronic acid (18 mg) in N,N-dimethyl-formamide (2 mL) a 2 M aqueous Na2CO3 solution (0.125 mL) is added. The mixture is sparged with argon and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (8.2 mg) is added. The resulting mixture is stirred over night at 90° C. After cooling to room temperature, the mixture is filtered through basic alumina, washed with DMF/MeOH (9:1) and concentrated. The residue is purified by preparative HPLC (eluent water (+0.1% TFA)/MeOH) to yield the desired product. HPLC (method 8): tR=1.95 min; Mass spectrum (ESI+): m/z=391 [M+H]+.

Workup

  1. additionis added
  2. customThe mixture is sparged with argon and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (8.2 mg)
  3. additionis added
  4. temperatureAfter cooling to room temperature
  5. filtrationthe mixture is filtered through basic alumina
  6. washwashed with DMF/MeOH (9:1)
  7. concentrationconcentrated
  8. customThe residue is purified by preparative HPLC (eluent water (+0.1% TFA)/MeOH)

Sources & evidence

ORD record
ord-b6684eb71bb848558723f4b65a274080
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

Loading…