Ethyl chloroacetate → HCID 67158215, compound

HRID 549042Notes

Reaction equation

HRID 549042 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[N:20]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH:13]=1.[H-].[Na+].Cl[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C)C=O>[CH2:38]([O:37][C:35](=[O:36])[CH2:34][N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[C:6]([C:12]2[N:20]([S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH:13]=2)=[CH:7]1)[CH3:39]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 22477257HCID 22477257, compound

Product 1

HCID 67158215HCID 67158215, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [6.6 g, Reference Example 12(a)] in dimethylformamide (100 mL), under a nitrogen atmosphere, was treated with sodium hydride (700 mg, 60% dispersion in oil). After stirring at ambient temperature for 30 minutes the mixture was treated dropwise with ethyl chloroacetate (2.0 mL, 23.75 mmol) and stirring was continued for an additional 4 hours. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, then dried over sodium sulfate and then evaporated to give the title compound (5.77 g) as a yellow solid, MS: 504 (MH+). HPLC (METHOD A): RT=11.88 minutes.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 4 hours
  3. customThe reaction mixture was evaporated
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-f914f03e9c43454584360f6c13549b26
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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