Pyridine → HCID 178510973, compound

HRID 2289968Notes

Reaction equation

HRID 2289968 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])=[CH:15][C:14]=3[F:28])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.N1C=CC=CC=1>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])=[CH:15][C:14]=3[F:28])=[O:9])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 178510972HCID 178510972, compound

Product 1

HCID 178510973HCID 178510973, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of the title compound of Example 89 (0.11 g) in 25 mL EtOAc is added triethylamine (0.08 mL) and pyridine (5 mL) to aid dissolution. After 10% Pd/C (50 mg) is added, the reaction is placed under a hydrogen balloon. After 2 hours, the reaction is complete and subsequently filtered over Celite. The filter cake is washed with ethyl acetate. The filtrate is concentrated to give a tan solid which is further dried on the vacuum pump to afford the desired product (0.088 g).

Workup

  1. dissolutiondissolution
  2. filtrationsubsequently filtered over Celite
  3. washThe filter cake is washed with ethyl acetate
  4. concentrationThe filtrate is concentrated
  5. customto give a tan solid which
  6. customis further dried on the vacuum pump

Sources & evidence

ORD record
ord-58ea07bdfaf3436db976995c05ab4979
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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