Sodium t-butoxide → HCID 178454100, compound

HRID 707232Notes

Reaction equation

HRID 707232 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]1[CH2:11][C@H:10]([NH:12][C:13](=[O:24])[C:14]([C:17]2[C:18](Cl)=[N:19][CH:20]=[CH:21][CH:22]=2)([CH3:16])[CH3:15])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+]>O1CCOCC1>[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[C:14]([CH3:16])([CH3:15])[C:13]2=[O:24])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 178454120HCID 178454120, compound

Product 1

HCID 178454100HCID 178454100, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Tert-butyl(trans-3-(2-(2-chloropyridin-3-yl)-2-methylpropanamido)cyclobutyl)carbamate (1074 mg, 2.92 mmol), sodium t-butoxide (561 mg, 5.84 mmol), and chloro(2-dicyclohexylphosphino-2′,6′-di-1-propoxy-1,1′-biphenyl)[2-(2-aminoethyl-phenyl)]palladium(ii) methyl tert-butyl ether adduct (143 mg, 0.175 mmol) were sealed in a round-bottomed flask under nitrogen. Dry dioxane (5 mL) was added and the reaction heated at 80° C. After 2 hours, the mixture was cooled and partitioned between ethyl acetate, water, and saturated ammonium chloride. The organic was dried with magnesium sulfate and evaporated to dryness to give tert-butyl(trans-3-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutyl)carbamate (980 mg, 2.96 mmol, quantitative) as light-yellow solid.

Workup

  1. temperaturethe mixture was cooled
  2. custompartitioned between ethyl acetate, water, and saturated ammonium chloride
  3. dry with materialThe organic was dried with magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-41c14b8f15434fa48b31678d17b8996f
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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