HCID 59529757, compound → HCID 59529784, compound

HRID 1952343Notes

Reaction equation

HRID 1952343 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15](/[CH:17]=[CH:18]/[C:19]3[C:27]4[C:22](=[N:23][C:24]([F:28])=[CH:25][CH:26]=4)[N:21]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[N:20]=3)[N:14]=[C:13]([O:38][CH3:39])[C:12]=2[Cl:40])[CH:9]=1)[C:5]#[N:6].[H][H]>C1COCC1.CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([CH2:17][CH2:18][C:19]3[C:27]4[C:22](=[N:23][C:24]([F:28])=[CH:25][CH:26]=4)[N:21]([CH2:29][C:30]4[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=4)[N:20]=3)[N:14]=[C:13]([O:38][CH3:39])[C:12]=2[Cl:40])[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 2

HCID 59529757HCID 59529757, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59529784HCID 59529784, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Compound 4-1 (400 mg; 0.694 mmol) was dissolved in 6 mL THF/MeOH (1:1) and the system purged with nitrogen (3×). 10% Pd/C (739 mg; 0.694 mmol) was then added to the reaction mixture which was then purged (3×) with nitrogen and then with hydrogen (3×). The purged reaction mixture then remained under atmospheric pressure of hydrogen for 4 hours at room temperature. The reaction mixture was then filtered through celite and concentrated. The crude product was then purified by flash chromatography (40-100% EtOAc in hexane) to give the title compound. MS M+1: 577.6. 1H NMR (CDCl3): 2.12 (t, 2H), 3.32 (t, 2H), 3.76 (s, 3H), 3.90 (s, 3H), 5.53 (s, 2H), 6.30 (s, 1H), 6.65 (d, 1H), 6.68 (d, 2H), 7.08 (m, 1H), 7.12 (m, 1H), 7.20 (d, 2H), 7.42 (m, 1H), 7.94 (t, 1H).

Workup

  1. customthe system purged with nitrogen (3×)
  2. customwas then purged (3×) with nitrogen
  3. customThe purged reaction mixture
  4. filtrationThe reaction mixture was then filtered through celite
  5. concentrationconcentrated
  6. customThe crude product was then purified by flash chromatography (40-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-5d233885baac4aac8582a94901f18e7f
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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