Toluene → N-((S)-6-Pyridin-3-yl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

HRID 1913819Notes

Reaction equation

HRID 1913819 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:27])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[CH:16][CH:15]=1)[CH2:6][CH2:5]2.C1(C)C=CC=CC=1.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37](B(O)O)[CH:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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.C(O)C>[N:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH2:8][C@@H:7]([NH:12][C:13](=[O:27])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]4[CH2:26][CH2:25][CH2:24][O:23]4)=[CH:16][CH:15]=2)[CH2:6][CH2:5]3)[CH:36]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 27343783-Pyridinylboronic acidHCID 67545579N-((S)-6-Bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Product 1

HCID 67544347N-((S)-6-Pyridin-3-yl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (1.00 g), toluene (10 ml) and Pd(PPh3)4 (2.69 g) was admixed with 3-pyridylboronic acid (0.28 g), ethanol (3 ml) and cesium carbonate solution (1.2 ml; 2 M in water). The mixture was boiled at reflux for 7 hours. The cooled reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was washed with sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel. The product was thus obtained with the molecular weight of 428.54 (C27H28N2O3); MS (ESI): 429 (M+H+).

Workup

  1. temperatureat reflux for 7 hours
  2. customThe cooled reaction mixture
  3. washwashed with water
  4. washThe organic phase was washed with sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel
  8. customThe product was thus obtained with the molecular weight of 428.54 (C27H28N2O3)

Sources & evidence

ORD record
ord-b99976bca4f34394aedcc9c9c4d5f2b1
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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