Ethanol → HCID 58355420, compound

HRID 1509594Notes

Reaction equation

HRID 1509594 reaction equation
Br[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH3:12])[C:5]([C:13]([N:15]([CH2:37][CH:38]([CH3:40])[CH3:39])[C@H:16]2[CH2:21][C@@H:20]([C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[CH2:19][N:18]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:17]2)=[O:14])=[CH:4][CH:3]=1.[N:41]1[CH:46]=[CH:45][CH:44]=[C:43](B(O)O)[CH:42]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>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.O.C1(C)C=CC=CC=1>[CH3:12][O:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:2]([C:43]2[CH:42]=[N:41][CH:46]=[CH:45][CH:44]=2)=[CH:3][CH:4]=[C:5]1[C:13]([N:15]([CH2:37][CH:38]([CH3:39])[CH3:40])[C@H:16]1[CH2:21][C@@H:20]([C:22]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:23])[CH2:19][N:18]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH2:17]1)=[O:14]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 58355282HCID 58355282, compound

Product 1

HCID 58355420HCID 58355420, compoundYield 106.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl (3S,5R)-3-[{[5-bromo-1-(4-methoxybutyl)-1H-pyrrol-2-yl]carbonyl}(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (188 mg), pyridin-3-ylboronic acid (41 mg), tetrakis(triphenylphosphine)palladium(0) (35 mg), sodium carbonate (371 mg), ethanol (2 ml), toluene (2 ml) and water (2 ml) was heated under reflux for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:1-1:0) was concentrated under reduced pressure, and crystals were collected by filtration to give the object product (200 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washa fraction eluted with ethyl acetate-hexane (1:1-1:0)
  8. concentrationwas concentrated under reduced pressure, and crystals
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-531d5e0e49ac4fb995ff819e7ee95f63
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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