2H-Indol-2-one, 1,3-dihydro-7-methyl- → 5-(6-Chloro-pyrimidine-4-carbonyl)-7-methyl-1,3-dihydro-indol-2-one

HRID 469359Notes

Reaction equation

HRID 469359 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[CH3:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18](=[O:21])[CH2:17]2.[Cl-].[Cl-].[Cl-].[Al+3]>CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([C:14]2[CH:15]=[C:16]3[C:20](=[C:12]([CH3:11])[CH:13]=2)[NH:19][C:18](=[O:21])[CH2:17]3)=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 30142252H-Indol-2-one, 1,3-dihydro-7-methyl-HCID 6451240Aluminum(III) ChlorideHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 581811435-(6-Chloro-pyrimidine-4-carbonyl)-7-methyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.92 g (10.9 mmol) 6-chloropyrimidine-4-carboxylic acid chloride, 1.60 g (10.9 mmol) 7-methyl-1,3-dihydro-indol-2-one and 7.33 g (55.0 mmol) aluminium trichloride were heated to 130° C. for 3 h with stirring. The mixture was combined first with ice water and then with EtOAc. The precipitate formed as black flakes was suction filtered and the phases were separated. The aqueous phase was extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, filtered and evaporated down i. vac.

Workup

  1. customThe precipitate formed as black flakes
  2. filtrationfiltered
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted several times with EtOAc
  5. customThe combined organic phases were dried on sodium sulphate
  6. filtrationfiltered
  7. customevaporated down i

Sources & evidence

ORD record
ord-6479643787ae47c59e586dda64d16ad0
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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