Ethanol → 6-[6-(4-Dimethylamino-phenyl)-1,2,3,4-tetrahydro-carbazol-9-yl]-hexanoic acid ethyl ester

HRID 403648Notes

Reaction equation

HRID 403648 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[CH3:2].[CH2:25](O)[CH3:26].C([O-])([O-])=O.[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[C:14]([C:26]1[CH:25]=[CH:16][C:11]([N:10]([CH3:22])[CH3:9])=[CH:12][CH:13]=1)[CH:15]=2)[CH3:2]

Participants

7

Reactant 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 668733756-(6-Bromo-1,2,3,4-tetrahydro-carbazol-9-yl)-hexanoic acid ethyl ester2×

Product 1

HCID 668904806-[6-(4-Dimethylamino-phenyl)-1,2,3,4-tetrahydro-carbazol-9-yl]-hexanoic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalyst2×HCID 1140TolueneSolvent

Procedure

4-Dimethylamino boronic acid (0.221 g, 1.34 mmol), tetrabutylammonium bromide (TBAB) (0.049 g, 1.25 mmol), palladium acetate (Pd(OAc)2 (0.017 g, 0.08 mmol), triorthotoluene phosphine (P(o-toluene)3 (0.035 g, 0.12 mmol), and 6-(6-bromo-1,2,3,4-tetrahydro-carbazol-9-yl)-hexanoic acid ethyl ester (compound 4) (0.300 g, 0.76 mmol) were added to a flask, dissolved in toluene (3 mL), ethanol (2 mL), and 2M Na2CO3 (1 mL), and stirred overnight at 70° C. Compound 32 was purified by column chromatography to give 310 mg of the product as a solid.

Workup

  1. customCompound 32 was purified by column chromatography

Sources & evidence

ORD record
ord-ef44d3eaa2674caa89a99ff5ea271950
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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