Potassium Carbonate → HCID 58742408, compound

HRID 722190Notes

Reaction equation

HRID 722190 reaction equation
B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+].Br[C:26]1[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[C:28]([O:34][CH3:35])[CH:27]=1.Br[C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]([C@@H:46]2[CH:51]3[CH2:52][CH2:53][N:48]([CH2:49][CH2:50]3)[CH2:47]2)=[O:45])=[CH:39][CH:38]=1.[OH-].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:33][CH2:32][C:29]1[CH:30]=[CH:31][C:26]([C:37]2[CH:42]=[CH:41][C:40]([NH:43][C:44]([C@@H:46]3[CH:51]4[CH2:52][CH2:53][N:48]([CH2:49][CH2:50]4)[CH2:47]3)=[O:45])=[CH:39][CH:38]=2)=[CH:27][C:28]=1[O:34][CH3:35]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 2733548Bis(pinacolato)diboraneHCID 151282434-Bromo-2-methoxybenzyl alcoholHCID 58742393(3R)-N-(4-bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide

Product 1

HCID 58742408HCID 58742408, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

118 mg (0.47) of bis(pinacolato)diboron, 193 mg (1.4 mmol) of dry potassium carbonate, and (4-bromo-2-methoxyphenyl)methanol are dissolved in 1 ml of DMF. Argon is passed through the reaction mixture for 15 minutes, and then 14.2 mg (0.02 mmol) of PdCl2(dppf) are added, and the mixture is heated at 85° C. overnight. Then, 120 mg (0.39 mmol) of (3R)-N-(4-bromophenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide, 1.94 ml of 1N sodium hydroxide solution and a further 14.2 mg (0.02 mmol) of PdCl2(dppf) are added. The mixture is heated at 85° C. overnight. The solvent is removed under reduced pressure. The crude product is purified by chromatography on silica gel 60 (mobile phase: dichloromethane→dichloromethane/methanol/ammonia 60:40:2). The solvent is stripped off under reduced pressure, and final residues of solvent are removed under high vacuum. 5 mg (4% of theory) of the title compound are obtained.

Workup

  1. temperatureThe mixture is heated at 85° C. overnight
  2. customThe solvent is removed under reduced pressure
  3. customThe crude product is purified by chromatography on silica gel 60 (mobile phase: dichloromethane→dichloromethane/methanol/ammonia 60:40:2)
  4. customare removed under high vacuum

Sources & evidence

ORD record
ord-e7e00d8390e5451aa8e7ca1b7d237ef5
Source dataset
uspto-grants-2006_11
Patent number
US07138410B2

Reaction notes

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