Hydroxide → Ammonia

HRID 969298Notes

Reaction equation

HRID 969298 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](B(O)O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl-].[Li+].C(=O)([O-])[O-].[K+].[K+].[CH2:21](O)[CH2:22][CH2:23]O.[OH-].CO[CH2:29][CH2:30]OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH3:1].[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:22]3[CH2:23][CH:30]4[N:1]([CH3:9])[CH:2]([CH2:3][CH2:29]4)[CH:21]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

9

Reactant 6

HCID 961HydroxideHCID 80711,2-DimethoxyethaneHCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 27343615-Indolylboronic acid

Product 2

HCID 222AmmoniaHCID 9878053HCID 9878053, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of (±)-8-methyl-3-trifluoromethanesulfonyl-oxy-8-azabicyclo[3.2.1]oct-2-ene (3.37 g, 12.4 mmol), 5-indolylboronic acid (2.00 g, 12.4 mmol), lithium chloride (1.58 g, 37.3 mmol), tetrakistriphenylphosphinepalladium(0) (0.43 mg, 0.4 mmol), potassium carbonate (5.14 g, 37.3 mmol), 1,3-propandiol (2.84 g, 37.3 mmol) and 1,2-dimethoxyethane (40 ml) was stirred and heated at reflux for 20 hours. Aqueous odium hydroxide (100 ml, 1 M) was added. The mixture was extracted twice with diethyl ether. Chromatography of this crude mixture on silica gel with dichloromethane, ethanol and conc. ammonia (89:10:1) gave the title compound. The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Yield 130 mg, 3.0%. Mp 167.4-178.0° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 hours
  3. extractionThe mixture was extracted twice with diethyl ether

Sources & evidence

ORD record
ord-72752975abf3434aba55a50eb44dbd06
Source dataset
uspto-grants-2007_12
Patent number
US07307087B2

Reaction notes

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