Methanol → Ethyl 7-(2-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate
Reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[CH2:12][CH2:11][C:10](=O)[N:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2=[N:6][C:7]=1[Cl:8].O1CCCC1.B.CO>O1CCCC1>[Br:1][C:2]1[N:3]=[C:4]2[CH2:12][CH2:11][CH2:10][N:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]2=[N:6][C:7]=1[Cl:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of ethyl 7-(2-bromo-3-chloro-6-oxo-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 1) (1.0 g, 2.388 mmol) in tetrahydrofuran (10 ml) under a nitrogen atmosphere at 0° C. was treated slowly with 1M borane tetrahydrofuran complex (11.94 ml, 11.94 mmol) and the resultant solution was stirred at 0° C. for 30 minutes and then allowed to warm to room temperature. The mixture was cooled to 0° C. and treated with borane tetrahydrofuran complex borane (2.4 ml, 2.4 mmol). Once the addition was complete the mixture was stirred at 0° C. for 30 minutes and then at RT. The mixture was cooled in ice and carefully treated with MeOH. The mixture was stirred at room temperature for 1 hour and then evaporated under vacuum to give an oil which was purified by chromatography on silica eluting with 0-100% EtOAc/iso-hexane to afford the title compound;
Workup
- temperatureThe mixture was cooled to 0° C.
- additionOnce the addition
- customat RT
- temperatureThe mixture was cooled in ice
- stirringThe mixture was stirred at room temperature for 1 hour
- customevaporated under vacuum
- customto give an oil which
- customwas purified by chromatography on silica eluting with 0-100% EtOAc/iso-hexane
Sources & evidence
- ORD record
- ord-cdb690ac55b64630bb616df9b93f8edc
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754085B2
Reaction notes
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