Diethylamine → HCID 59442033, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2.Br[CH2:16][C:17](Cl)=[O:18].C([O-])([O-])=O.[K+].[K+].[NH:26]([CH2:29][CH3:30])[CH2:27][CH3:28]>C1COCC1.CCOC(C)=O>[CH2:27]([N:26]([CH2:29][CH3:30])[CH2:16][C:17]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:6][CH2:7]1)=[O:18])[CH3:28]Participants
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (Intermediate B99, 433 mg, 2.23 mol), bromoacetyl chloride (386 mg, 2.45 mmol) and K2CO3 (924 mg, 6.69 mmol) in THF (50 mL) was stirred for 40 min and then Et2NH (326 mg, 4.46 mmol) was added. The reaction mixture was stirred for 1 day, additional Et2NH (0.3 mL) was added, stirring was continued for an additional 24 h, then the reaction was heated at 60° C. for 2 h. The resulting mixture was diluted with EtOAc (200 mL), washed with water (150 mL) and a saturated NaCl solution (100 mL), and back extracted with EtOAc (100 mL). The organic layers were combined, dried (Na2SO4), and concentrated to obtain N,N-diethyl-2-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine (687 mg, 100%). ESIMS (M+H)+=307.97.
Workup
- stirringThe reaction mixture was stirred for 1 day
- stirringstirring
- waitwas continued for an additional 24 h
- washwashed with water (150 mL)
- extractiona saturated NaCl solution (100 mL), and back extracted with EtOAc (100 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fa266c7a725c4ac2a3e0d096008477e7
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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