Sodium ethoxide → HCID 22859565, compound

HRID 1441062Notes

Reaction equation

HRID 1441062 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17].C(B(CC)[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)C.[O-]CC.[Na+].[Br-].C([NH3+])CCC>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:17][N:13]1[CH2:14][CH2:15][CH2:16][C@@H:12]1[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH:3]=2)[NH:7][CH:6]=1

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 11185464(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indoleHCID 133188714-(Diethylboranyl)pyridineHCID 21904131N-butyl-ammonium bromide

Product 1

HCID 22859565HCID 22859565, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

5-Bromo-3-(1-methylpyrrolidin-2(R)-ylmethyl)-1H-indole (see Preparation 36) and diethyl (4-pyridyl)borane (see Preparation 50) were reacted together in the presence of sodium ethoxide, n-butylammonium bromide and tetrakis(triphenylphosphine)palladium(O) using a procedure similar to that in Example 56. This gave the title compound. Found: C,75.77; H,7.16; N,13.78%; C19H21N3.1/8CH2Cl2 requires: C,76.06; H,7.09; N,13.91%.

Sources & evidence

ORD record
ord-7853c0fe6f1e44ffb8b2a13f712edb85
Source dataset
uspto-grants-1996_03
Patent number
US05502065

Reaction notes

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