Sodium hydride → HCID 118177559, compound

HRID 628268Notes

Reaction equation

HRID 628268 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[NH:13][C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1.[CH3:17][CH2:18][O:19][C:20]([CH:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>CN(C=O)C.CCOC(C)=O.O>[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[N:13]([CH:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:20]([O:19][CH2:18][CH3:17])=[O:21])[C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 97780Ethyl bromophenylacetateHCID 1369631111,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 118177559HCID 118177559, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (110 mg, 2.7 mmol, 60% in mineral oil) was added to a solution of 1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (0.500 g, 2.68 mmol, from Example 2, Step 5) in DMF (50 mL). After 15 minutes, a solution of ethyl-alpha-bromophenyl acetate (0.70 mL, 4.0 mmol, Aldrich) in DMF (10 mL) was added dropwise. The mixture was stirred for 15 minutes at room temperature and then was poured into pH 7 buffer and diluted with EtOAc and water. The layers were separated and the aqueous was extracted again with EtOAc. The combined organic extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 5-10% MeOH in DCM (187 mg, 20%).

Workup

  1. additionwas poured into pH 7 buffer
  2. customThe layers were separated
  3. extractionthe aqueous was extracted again with EtOAc
  4. washThe combined organic extracts were washed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by flash chromatography
  9. washeluting with a gradient from 5-10% MeOH in DCM (187 mg, 20%)

Sources & evidence

ORD record
ord-69ad66c8f4df405eb3b69df97c8c08a0
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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