Diiodomethane → HCID 22292780, compound
Reaction equation
[CH2:1]([Zn]CC)[CH3:2].FC(F)(F)C(O)=O.ICI.[F:16][C:17]([F:35])([F:34])[C:18]([N:20]1[CH2:26][C:25](=[CH2:27])[C:24]2[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:23]=2[CH2:22][CH2:21]1)=[O:19]>ClCCl>[F:35][C:17]([F:16])([F:34])[C:18]([N:20]1[CH2:26][CH:25]([CH:27]2[CH2:2][CH2:1]2)[C:24]2[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:23]=2[CH2:22][CH2:21]1)=[O:19]Participants
Procedure
A solution of diethyl zinc (1 mL, 1 M in hexanes) in dichloromethane (1 mL) at 0 C. was treated with trifluoroacetic acid in dichloromethane (0.5 mL) and the mixture stirred for 15 min. Diiodomethane (0.280 g, 1.0 mmol) in dichloromethane (0.5 mL) was then added and stirred for 15 minutes. N-Trifluoroacetyl-7-methoxy-1-methylene-2,3,4,5-tetrahydro-1H-3-benzazepine (0.075 g, 0.26 mmol) in dichloromethane (1 mL) was added and the mixture stirred for 30 minutes at 0 C. and then for 2 hours at 20 C. The product mixture was quenched with aqueous saturated NH4Cl (5 mL), extracted to twice with CH2Cl2 (20 mL), washed with saturated aqueous NaHCO3 (10 mL), washed with H2O (10 mL), and concentrated. Flash chromatography (7% EtOAc in hexanes, silica) resulted in 0.050 g of a white solid. MS calculated for C15H16F3NO2+H: 300, observed: 300.
Workup
- stirringstirred for 15 minutes
- stirringthe mixture stirred for 30 minutes at 0 C
- waitand then for 2 hours at 20 C
- customThe product mixture was quenched with aqueous saturated NH4Cl (5 mL)
- extractionextracted to twice with CH2Cl2 (20 mL)
- washwashed with saturated aqueous NaHCO3 (10 mL)
- washwashed with H2O (10 mL)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2319df6681704a9d88e1f56b547c6900
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273734B1
Reaction notes
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