Iodoethane → HCID 9834404, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:12])[NH:11][C:5]=2[CH:4]=1.I[CH2:16][CH3:17].[H-].[Na+]>>[CH2:16]([N:11]1[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:14]=[CH:13][C:6]=2[CH2:7][CH2:8][CH2:9][C:10]1=[O:12])[CH3:17]Participants
4
Procedure
As shown in Scheme 3, 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (3A) was alkylated using iodoethane as an alkylating reagent and one equivalent of sodium hydride as a base to provide 1-ethyl-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (9A). A bromination in methanol at ambient temperature using bromine as a brominating agent afforded exclusively 7- bromo regioisomer (10A) which was transformed further employing a catalytic cross coupling methodology. This coupling reaction was conveniently carried out by use of 4-methylpiperazine as a reagent, BINAP as a chelating reagent, palladium acetate as a catalyst in the presence of cesium carbonate as a base.
Sources & evidence
- ORD record
- ord-79f068b138104e34b1f38e782680ea4b
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06514965B1
Reaction notes
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