1,2-Diaminocyclohexane, trans- → HCID 11244171, compound

HRID 746832Notes

Reaction equation

HRID 746832 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[CH:2]1.Br[C:13]1[CH:14]=[CH:15][C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[C:17]([CH:20]=1)[C:18]#[N:19].CC(C)([O-])C.[Na+].N[C@@H]1CCCC[C@H]1N>CN(C=O)C.CCOC(C)=O.CCCCCC>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:16]1[CH:15]=[CH:14][C:13]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=3)=[CH:2]2)=[CH:20][C:17]=1[C:18]#[N:19]

Participants

8

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 8203972-(1H-pyrrol-3-yl)PyridineHCID 23676156Sodium t-butoxideHCID 69303601HCID 69303601, compound

Product 1

HCID 11244171HCID 11244171, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

2-(1H-Pyrrol-3-yl)pyridine (300 mg, 2.0 mmol), 5-bromo-2-pyridin-2-ylbenzonitrile (538.7 g, 2.0 mmol), sodium tert-butoxide (384 mg, 4.0 mmol) and trans-1,2 diaminocyclohexane (23 mg, 0.2 mmol) were combined in DMF (10 mL) under argon. The reaction mixture was heated at 140° C. overnight. The reaction mixture was allowed to cool to ambient temperature. TLC analysis showed no starting material present. The reaction mixture was diluted with EtOAc (100 mL), and washed with H2O (3×100 mL), brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford a dark oil. The crude product was purified by column chromatography eluting with 5.5:4.5 EtOAc:Hexane to afford 2-pyridin-2-yl-5-(3-pyridin-2-yl-1H-pyrrol-1-yl)benzonitrile (160 mg, 27% yield) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ 8.73-8.74 (d, 1H), 8.48-8.49 (d, 1H), 8.14-8.15 (d, 1H), 7.98-8.01 (m, 3H), 7.92-7.94 (d, 1H), 7.86-7.88 (d, 1H), 7.79-7.81 (t, 1H), 7.47-7.53 (m, 2H), 7.22-7.24 (m, 1H), 6.94-6.95 (m, 1H). MS 323.4 (M++H).

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed with H2O (3×100 mL), brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a dark oil
  7. customThe crude product was purified by column chromatography
  8. washeluting with 5.5:4.5 EtOAc

Sources & evidence

ORD record
ord-d7c9582b6c2e4841aa1ac9d3c528d31a
Source dataset
uspto-grants-2008_07
Patent number
US07393959B2

Reaction notes

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