Ethanol → HCID 58355438, compound

HRID 1509595Notes

Reaction equation

HRID 1509595 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.N1C=CC=CC=1B(O)O.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[CH:2]=[CH:3][CH:4]=[C:5]1[C:13]([N:15]([CH2:37][CH:38]([CH3:40])[CH3:39])[C@H:16]1[CH2:21][C@@H:20]([C:22]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[O:23])[CH2:19][N:18]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:17]1)=[O:14]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2762745Pyridine-2-boronic acidHCID 58355282HCID 58355282, compound

Product 1

HCID 58355438HCID 58355438, compoundYield 124.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

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 (220 mg), pyridin-2-ylboronic acid (65 mg), sodium carbonate (370 mg), tetrakis(triphenylphosphine)palladium (40 mg), ethanol (2 ml), toluene (2 ml) and water (2 ml) was stirred at 80° C. for 12 hr. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate-water, and the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. 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 to give the object product (240 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate-water
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane (1:1-1:0)
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a7f145c74b14c15a64714617ad7bd1b
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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