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Cesium carbonate → HCID 68670654, compound

HRID 2298043
Notes
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Reaction equation

HRID 2298043 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[N:14]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:13][C:5]1[CH:4]=[CH:3][C:2]([N:17]2[CH2:18][CH2:19][CH2:20][N:14]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][CH2:16]2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 144749Ethyl 5-bromo-2-chlorobenzoateHCID 634876Binap, (A+-)-HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 68670654HCID 68670654, compoundYield 28.9%

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-2-chloro-benzoic acid, ethyl ester (0.50 g), hexahydro-1H-1,4-diazepine-1-carboxylic acid, 1,1-dimethylethyl ester (0.46 g), cesium carbonate (0.86 g), palladium (II) acetate (8.5 mg) and (R)-BINAP (35 mg) in toluene (3 ml) was heated at 100° C. for 14 h in a pressure vessel flushed with nitrogen. The cooled reaction mixture was poured into water and extracted (3 times) with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution and then dried over magnesium sulfate. Evaporation under reduced pressure gave an oil which was purified by chromatography over silica gel, eluting with 20% ethyl acetate in iso-hexane to yield the subtitle compound as an oil (0.21 g).

Workup

  1. customflushed with nitrogen
  2. customThe cooled reaction mixture
  3. extractionextracted (3 times) with ethyl acetate
  4. washThe combined organic extracts were washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation under reduced pressure
  7. customgave an oil which
  8. customwas purified by chromatography over silica gel
  9. washeluting with 20% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-89db27d8275a4d948ca2286c38e91ac9
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06492355B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes