Methanol → HCID 59835738, compound

HRID 1916768Notes

Reaction equation

HRID 1916768 reaction equation
C([O-])(O)=O.[Na+].O.O.[Sn](Cl)Cl.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]#[C:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[C:28]([N+:40]([O-])=O)[CH:27]=3)=[N:22][CH:23]=2)=[CH:14][CH:13]=1.CO>CCOC(C)=O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]#[C:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]4[CH2:36][CH2:37][CH2:38][CH2:39]4)=[C:28]([NH2:40])[CH:27]=3)=[N:22][CH:23]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 61436Stannous chloride dihydrate2×HCID 516892Sodium Bicarbonate2×HCID 10049301HCID 10049301, compound

Product 1

HCID 59835738HCID 59835738, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

200 mg (2.5 mmol) NaHCO3 and 300 mg (1.1 mmol) tin-(II)-chloride dihydrate are added to a solution of 100 mg (0.22 mmol) 5-(4-chloro-phenyl)-2-[3-nitro-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine (Example 3.13) in 10 mL EtOAc and the reaction mixture is refluxed for 2 h. To complete the reaction a further 200 mg (2.5 mmol) NaHCO3, 300 mg (1.1 mmol) tin-(II)-chloride dihydrate and 1 mL MeOH are added and the mixture is refluxed for a further 2 h. After cooling, 4 g of silica gel are added, the solvent is eliminated i.vac. and the residue is purified by chromatography (silica gel, DCM/MeOH/NH3 8:2:0.2).

Workup

  1. temperaturethe reaction mixture is refluxed for 2 h
  2. additionare added
  3. temperaturethe mixture is refluxed for a further 2 h
  4. temperatureAfter cooling
  5. addition4 g of silica gel are added
  6. customand the residue is purified by chromatography (silica gel, DCM/MeOH/NH3 8:2:0.2)

Sources & evidence

ORD record
ord-7d714ae615a849d0ae5919a6d443c4b8
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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