Triethylamine → HCID 68428921, compound

HRID 642273Notes

Reaction equation

HRID 642273 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:33])=[C:8]2[C:14]([Br:15])=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:12]([CH2:23][C:24]3[CH:32]=[CH:31][C:27]4[O:28][CH2:29][O:30][C:26]=4[CH:25]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[CH3:34][C:35]([CH3:40])([CH3:39])[C:36](Cl)=[O:37].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:33][C:36](=[O:37])[C:35]([CH3:40])([CH3:39])[CH3:34])=[C:8]2[C:14]([Br:15])=[C:13]([C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[N:12]([CH2:23][C:24]3[CH:32]=[CH:31][C:27]4[O:28][CH2:29][O:30][C:26]=4[CH:25]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 68428645HCID 68428645, compound

Product 1

HCID 68428921HCID 68428921, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension mixture of 1-benzo[1,3]dioxol-5-ylmethyl-3-bromo-2-(4-chloro-phenyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (320 mg, 0.60 mmol)(from Example 35(e)) in CH2Cl2 (3 mL) at 0° C. was added 2,2-dimethyl-propionyl chloride (87.4 mg, 0.73 mmol) and triethylamine (122 mg, 1.20 mmol). Resulting mixture was stirred at room temperature for 1.5 h. It was diluted with CH2Cl2 and washed with 0.1 N HCl aqueous solution, water and brine. The organic layer was dried over MgSO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (eluting with 5%-20% EtOAc in CH2Cl2) to give the title compound 361 mg. MS-(+)-ion: M+1=614.98, 613.02.

Workup

  1. customResulting mixture
  2. washwashed with 0.1 N HCl aqueous solution, water and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography (eluting with 5%-20% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-6e59522d4d9d4f94bddffb48a589fe84
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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