Potassium Carbonate → 2-(6-Chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester
Reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][CH3:9])=[C:4](I)[CH:3]=1.[C:11]([O:15][C:16]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1B(O)O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:11]([O:15][C:16]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1[C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=1[O:8][CH3:9])=[O:17])([CH3:14])([CH3:12])[CH3:13]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
Argon is passed for 30 min through a suspension of 135 mg 6-Chloro-4-iodo-3-methoxy-pyridazine, 130.5 mg 1-(tert-butoxycarbonyl)indole-2-boronic acid, 152 mg potassium carbonate, and 52.5 mg triphenylphosphine in 2.2 ml DME and 1.1 ml water. 11.2 mg palladium (II) acetate is added, and the mixture is stirred under reflux for 3 h. The product is isolated by extraction with ethyl acetate and purified by chromatography on silica gel yielding 80 mg 2-(6-Chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester
Workup
- temperatureunder reflux for 3 h
- custompurified by chromatography on silica gel yielding 80 mg 2-(6-Chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester
Sources & evidence
- ORD record
- ord-28d11d416310459daff1279f034bef16
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507734B2
Reaction notes
Loading…