Potassium Carbonate → HCID 68432245, compound

HRID 2090255Notes

Reaction equation

HRID 2090255 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:23][CH2:24][CH2:25][CH3:26])[N:14]([CH2:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][CH2:21][OH:22])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Br[CH2:28][C:29]1[CH:30]=[C:31]([CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH:32]=[CH:33][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:23][CH2:24][CH2:25][CH3:26])[N:14]([CH2:15][CH2:16][CH2:17][N:18]([CH2:28][C:29]3[CH:30]=[C:31]([CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH:32]=[CH:33][CH:34]=3)[CH2:19][CH2:20][CH2:21][OH:22])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10014651(3-Bromomethyl-phenyl)-acetic acid methyl esterHCID 68432501HCID 68432501, compound

Product 1

HCID 68432245HCID 68432245, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from step (vii) (2 g), methyl 2-(3-(bromomethyl)phenyl)acetate (1.4 g) and potassium carbonate (2.1 g) in DMF (20 mL) was stirred at rt under nitrogen for 24 h. The mixture was partitioned between DCM/water, the organics separated, washed with water, dried, and evaporated under reduced pressure. The residue was purified by chromotography on silica eluting with DCM/MeOH/Et3N (1000/50/3). Yield 2.43 g of solid.

Workup

  1. customThe mixture was partitioned between DCM/water
  2. washthe organics separated, washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromotography on silica eluting with DCM/MeOH/Et3N (1000/50/3)

Sources & evidence

ORD record
ord-56a30a890b68417f856f4e3f37b79492
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

Loading…