Water → HCID 46869361, compound

HRID 1628348Notes

Reaction equation

HRID 1628348 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:25])[C@@H:10]([NH:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].O>C(OCC)(=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.CN(C)C(=O)C>[O:25]=[C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:29]2[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=2)[CH:3]=1)[C@@H:10]([NH:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 67498417HCID 67498417, compound

Product 1

HCID 46869361HCID 46869361, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a 25 ml of flask was added ethyl 2-((S)-1-(3-bromophenylamino)-1-oxo-3-phenylpropan-2-ylamino)acetate 107.1.B (165 mg, 0.41 mmole), pyridine-4-yl boronic acid (53 mg, 0.43 mmole), tetrakis(triphenylphosphine)palladium (94 mg, 0.081 mmole), potassium carbonate (112 mg, 0.81 mmole), 0.2 ml of water and 2 ml of N,N-dimethylacetamide. The reaction mixture was stirred at 80° C. for 5 hours. Then, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After concentration in vacuo, the residue was chromatographed on silica gel to give 107.1.C (26 mg, 16% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.53 (s, 1H), 8.67 (d, J=5.8 Hz, 2H), 8.01 (s, 1H), 7.70-7.27 (m, 10H), 4.17-4.10 (m, 2H), 3.50 (dd, J=9.0, 4.3 Hz, 1H), 3.36 (s, 2H,), 3.35 (dd, J=14.1, 4.3 Hz, 1H), 2.92 (dd, J=14.1, 9.0 Hz, 1H), 1.99 (brs, 1H), 1.22 (t, J=7.2 Hz, 3H).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationAfter concentration in vacuo
  4. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-823a2af474ec4cf783729838c3376099
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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