Dimethylformamide → 6-Chloro-5-(4-(2-hydroxyethyl)-3-methoxyphenyl)-1h-indole-3-carbaldehyde
Reaction equation
[Cl-].ClC=[N+](C)C.CN([CH:10]=[O:11])C.[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][NH:19]2)=[CH:15][C:14]=1B1OCC(C)(C)CO1.Br[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][OH:39])=[C:33]([O:40][CH3:41])[CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>>[Cl:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([CH:10]=[O:11])=[CH:18][NH:19]2)=[CH:15][C:14]=1[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][OH:39])=[C:33]([O:40][CH3:41])[CH:32]=1Participants
6
Reactant 5
Product 1
Conditions
- Temperature
- 30 °C
Procedure
To a 0.4M solution of chlormethylene dimethylammonium chloride in DMF (7.5 mL, 3.8 mmol) was added 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (493 mg, 1.88 mmol). The mixture was stirred at 30° C. for 2 hrs. 0.50 mL of this solution (0.15 mmol) was placed in a vial with a 0.3M solution of 2-(4-bromo-2-methoxyphenyl)ethanol in DMF (0.50 mL, 0.15 mmol). 2M potassium carbonate (0.30 mL, 0.60 mmol) was then added and the mixture was purged with nitrogen. PddppfCl2 (9 mg, 0.01 mmol) was then added and the vial capped and heated to 90° C. for 3 hours. The reaction mixture was concentrated by Speedvac and purified via preparative TLC to give the title compound that was taken forward without further purification.
Workup
- customthe mixture was purged with nitrogen
- additionPddppfCl2 (9 mg, 0.01 mmol) was then added
- customthe vial capped
- temperatureheated to 90° C. for 3 hours
- concentrationThe reaction mixture was concentrated by Speedvac
- custompurified via preparative TLC
Sources & evidence
- ORD record
- ord-7ca502a1c01a4f7a9dbad1828c355557
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889730B2
Reaction notes
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