Hydrochloric Acid → HCID 59800134, compound
Reaction equation
B([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:7]=2)(O)O.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:25]1[N:30]=[CH:29][N:28]=[C:27](Cl)[CH:26]=1.O=O.[ClH:34]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:34][C:29]1[N:28]=[C:27]([C:4]2[NH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:7]=3)[CH:26]=[CH:25][N:30]=1Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
28 g (114 mmol) of 2-borono-5-ethoxycarbonylindole, 12 g (113 mmol) of sodium carbonate and 17.2 g of 2,4-(113 mmol) dichloropyrimidine were initially charged in 412 ml of ethanol. The clear solution was freed of oxygen by vigorous stirring and passing argon through (20 minutes). At RT, 2.67 g of tetrakis(triphenylphosphine)palladium(0) were added. The mixture was heated to from 65° C. to 70° C. for 2 hours (h). Subsequently, 112 ml of water and 112 ml of 30% hydrochloric acid were added and the mixture was cooled to 0° C. After filtration and drying under reduced pressure, 37.3 g (93% of theory) of ethyl 2-(2-chloropyrimidin-4-yl)-1H-indole-5-carboxylate were obtained (HPLC >96%).
Workup
- customthrough (20 minutes)
- temperatureThe mixture was heated to from 65° C. to 70° C. for 2 hours (h)
- filtrationAfter filtration
- customdrying under reduced pressure
Sources & evidence
- ORD record
- ord-07799abdaf0643c994312b7c07d58039
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546567B2
Reaction notes
Loading…