Ethanol → HCID 58585903, compound

HRID 656339Notes

Reaction equation

HRID 656339 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([C:20]([NH:22][CH:23]3[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]3)=[O:21])[CH2:15]2)=[N:12][CH:13]=1.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(C)C=CC=CC=1.C(O)C>O.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.C(OCC)(=O)C>[OH:29][CH:26]1[CH2:27][CH2:28][CH:23]([NH:22][C:20]([C@H:16]2[CH2:17][CH2:18][CH2:19][N:14]([C:11]3[CH:10]=[CH:9][C:8]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:13][N:12]=3)[CH2:15]2)=[O:21])[CH2:24][CH2:25]1

Participants

9

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58585885HCID 58585885, compound

Product 1

HCID 58585903HCID 58585903, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium carbonate (21.2 mg, 0.000200 mol) in water (0.10 mL) was added to a mixture of (3S)-1-(5-bromopyridin-2-yl)-N-(4-hydroxycyclohexyl)piperidine-3-carboxamide (38.2 mg, 0.000100 mol, prepared as example 154), phenylboronic acid (14.6 mg, 0.000120 mol) and tetrakis(triphenylphosphine)palladium(0) (3.5 mg, 0.0000030 mol) in toluene (200.0 μL, 0.001878 mol) and ethanol (100.0 μL, 0.001713 mol). The resulting mixture was irradiated with microwaves at 150° C. for 20 min. Ethyl acetate (5 mL) was added and the mixture was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in DMF and purified by prep.-HPLC to give the desired product. LCMS: m/z 380.2 (M+H)+.

Workup

  1. customThe resulting mixture was irradiated with microwaves at 150° C. for 20 min
  2. washthe mixture was washed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in DMF
  7. custompurified by prep.-HPLC

Sources & evidence

ORD record
ord-4e80227ebe224c189f1a8cc1e4887b9f
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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