Pyridine → HCID 72590893, compound

HRID 2301330Notes

Reaction equation

HRID 2301330 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([Br:28])=[C:12]([CH2:15][C:16]3[C:25]4[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=4)[CH2:19][CH2:18][N:17]=3)[CH:13]=2)[NH:8][C:7]=1[CH3:29])=[O:5])[CH3:2].N1C=CC=CC=1.[C:36](OC=O)(=[O:41])C(C)(C)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([Br:28])=[C:12]([CH:15]=[C:16]3[C:25]4[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=4)[CH2:19][CH2:18][N:17]3[CH:36]=[O:41])[CH:13]=2)[NH:8][C:7]=1[CH3:29])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11340023HCID 11340023, compoundHCID 11804789HCID 11804789, compound

Product 1

HCID 72590893HCID 72590893, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-bromo-5-(6-methoxy-3,4-dihydro-isoquinoline-1-ylmethyl)-2-methyl-1H-indole-3-carboxylic acid ethyl ester (2.03 g, 4.5 mmol) in CH2Cl2 (50 mL) is added pyridine (2.3 g, 30 mmol) and 3N formic pivalic anhydride (5 mL; 14.5 mmol) at 0° C., and the reaction is stirred at room temperature for 3 hours. CH2Cl2 (50 mL) is then added to the reaction mixture and the organic layer is washed with water (2×50 mL), IN HCl (50 mL), 1N NaOH (50 mL), and brine (50 mL). The solution is dried (Na2SO4), filtered, and concentrated in vacuo to give the desired product (1.3 g, 60%). MS: 483, 485 (M+1)+.

Workup

  1. washthe organic layer is washed with water (2×50 mL), IN HCl (50 mL)
  2. dry with materialThe solution is dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c4b85d918ec44ac982159534534419c
Source dataset
uspto-grants-2002_12
Patent number
US06500837B2

Reaction notes

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