Sodium Iodide → Methyl 4-(2-(2-aminoacetamido)thiophene-3-carbonyl)benzoate
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)=[O:8].[I-].[Na+].C(=O)=O.[NH3:24].[CH3:25][C:26](C)=[O:27]>O1CCCC1>[NH2:24][CH2:25][C:26]([NH:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)=[O:8])=[O:27]Participants
Conditions
- Temperature
- -78 °C
Procedure
In a 100 mL round-bottomed flask was dissolved title compound 491 (1 g, 2.96 mmol) and sodium iodide (0.533 g, 3.55 mmol) in tetrahydrofuran (20 mL) to give a yellow suspension. The mixture was heated at reflux for 2 hours. The mixture was cooled to −78° C. A Dewar-type condenser was attached and filled with dry ice/acetone Ammonia was introduced as a gas and about 30 mL was condensed into the flask. The reaction mixture was left to warm up to room temperature over the weekend. The solvent was removed in vacuo and the residue was purified via ISCO (50-100% EtOAc/Hexanes; 40 g silica gel column) to obtain product as a tan powder. The solid was purified by suspending it in 1:1 dichloromethane/ether and filtering to afford title compound 492 (265 mg, 28%) as a tan powder which was sufficiently pure for the next step. MS (m/z): 319.3 (M+H).
Workup
- customto give a yellow suspension
- temperatureThe mixture was heated
- temperatureat reflux for 2 hours
- additionwas introduced as a gas and about 30 mL
- customcondensed into the flask
- waitThe reaction mixture was left
- temperatureto warm up to room temperature over the weekend
- customThe solvent was removed in vacuo
- customthe residue was purified via ISCO (50-100% EtOAc/Hexanes; 40 g silica gel column)
- customto obtain product as a tan powder
- customThe solid was purified
- filtrationfiltering
Sources & evidence
- ORD record
- ord-d2acebff371249f1b2b53f26ef2aa78d
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193749B2
Reaction notes
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