Sodium Carbonate → 4-dimethylamino-4-phenyl-1-[3-(2-triethylsilanyl-1H-pyrrolo[3,2-c]pyridin-3-yl)propyl]cyclohexanol

HRID 2064522Notes

Reaction equation

HRID 2064522 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:7][C:6]([CH2:10][CH2:11][CH2:12][C:13]#[C:14][Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])([OH:9])[CH2:5][CH2:4]1.[NH2:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][C:31]=1I.C(=O)([O-])[O-].[Na+].[Na+]>O=O.C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd-2](Cl)C1C(Cl)=CC=CN=1)(C)C>[CH3:28][N:2]([CH3:1])[C:3]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:8][CH2:7][C:6]([CH2:10][CH2:11][CH2:12][C:13]2[C:31]3[CH:32]=[N:33][CH:34]=[CH:35][C:30]=3[NH:29][C:14]=2[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])([OH:9])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 15165104-Amino-3-iodopyridineHCID 1317299894-Dimethylamino-4-phenyl-1-(5-triethylsilanyl-pent-4-inyl)cyclohexanol

Product 1

HCID 686297494-dimethylamino-4-phenyl-1-[3-(2-triethylsilanyl-1H-pyrrolo[3,2-c]pyridin-3-yl)propyl]cyclohexanol

Reagents, catalysts & solvents 2

HCID 178439027HCID 178439027, compoundCatalystHCID 977OxygenSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-dimethylamino-4-phenyl-1-(5-triethylsilanyl-pent-4-inyl)cyclohexanol (741 mg, 1.85 mmol), 4-amino-3-iodopyridine (488 mg, 2.22 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride (PEPPSI, 251 mg, 0.37 mmol) and sodium carbonate (980 mg, 9.25 mmol) in oxygen-free N,N-dimethylformamide (10 mL) was stirred for 20 h at 100° C. The reaction mixture was then concentrated to low volume in a vacuum, the residue repeatedly taken up in toluol (10 mL) and each time concentrated to low volume again in a vacuum, this residue was taken up in ethyl acetate (30 mL) and water (30 mL) and the organic phase washed with water (2×15 mL) and sodium thiosulphate solution (2×25 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product was purified by means of flash chromatography (38 g, 20×2.5 cm) with ethyl acetate/methanol (4:1).

Workup

  1. concentrationThe reaction mixture was then concentrated to low volume in a vacuum
  2. concentrationeach time concentrated to low volume again in a vacuum
  3. washwater (30 mL) and the organic phase washed with water (2×15 mL) and sodium thiosulphate solution (2×25 mL)
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated to low volume in a vacuum
  6. customThe raw product was purified by means of flash chromatography (38 g, 20×2.5 cm) with ethyl acetate/methanol (4:1)

Sources & evidence

ORD record
ord-3eb6308ce66c49788cce29d2052fc55a
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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