Potassium Carbonate → N-(2-(adamantan-1-yl)ethyl)-2-fluoro-4-nitroaniline
Reaction equation
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2>CN(C=O)C>[C:21]12([CH2:20][CH2:19][NH:4][C:3]3[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=3[F:1])[CH2:22][CH:23]3[CH2:29][CH:27]([CH2:26][CH:25]([CH2:24]3)[CH2:30]1)[CH2:28]2Participants
5
Conditions
- Temperature
- 140 °C
Procedure
To a solution of 2-fluoro-4-nitroaniline (2.34 g, 15.0 mmol) in DMF (30 mL) were added K2CO3 (4.2 g, 30.4 mmol), KI (0.5 g, 3.01 mmol) and 1-(2-bromoethyl)adamantane (3.65 g, 15.0 mmol) and the mixture was stirred at 140° C. for 12 h. The mixture was then cooled to rt and filtered. The filtrate was diluted with 150 mL of DCM and washed with water (50 mL×3), brine (150 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1) to give the title compound as a yellow solid (477 mg, 10%).
Workup
- temperatureThe mixture was then cooled to rt
- filtrationfiltered
- additionThe filtrate was diluted with 150 mL of DCM
- washwashed with water (50 mL×3), brine (150 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1)
Sources & evidence
- ORD record
- ord-c8236c113979484cb19b56d02ecde0f1
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434695B2
Reaction notes
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