HCID 86610107, compound → HCID 178509911, compound

HRID 1157416Notes

Reaction equation

HRID 1157416 reaction equation
C(OC([N:8]1[C:12]2C=CC=N[C:11]=2[C:10]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([O:26][C:27]3[CH:32]=[C:31]([C:33]#[N:34])[CH:30]=[C:29]([Cl:35])[CH:28]=3)[CH:20]=2)=[N:9]1)=O)(C)(C)C>CCO.[Pd]>[Cl:35][C:29]1[CH:30]=[C:31]([CH:32]=[C:27]([O:26][C:21]2[CH:20]=[C:19]([CH2:18][CH2:17][C:10]3[C:11]4[C:12](=[N:8][CH:12]=[CH:11][CH:10]=4)[NH:8][N:9]=3)[CH:24]=[CH:23][C:22]=2[Cl:25])[CH:28]=1)[C:33]#[N:34]

Participants

4

Reactant 1

HCID 86610107HCID 86610107, compound

Product 1

HCID 178509911HCID 178509911, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 250 mg (0.50 mmol) of tert-butyl-3-{[4-chloro-3-(3-chloro-5-cyanophenoxy)phenyl]ethynyl}-1H-pyrazolo[3,4-]pyridine-1-carboxylate in 10 mL of absolute EtOH was hydrogenated at 1 atm pressure (balloon) over 250 mg of 10% Pd on carbon catalyst. After approximately 24 hours, the reaction mixture was filtered through a pad of Celite, and the filtrate concentrated in vacuo to a yellow oil. The crude intermediate oil was dissolved in 1 mL TFA, and the solution stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo to provide the crude product as a dark oil. The dark oil was purified by reversed phase preparative LC on a Gilson apparatus to give the desired product as a fluffy off-white solid. MS M+=409. 1H NMR (CDCl3): 3.17 (t, 2H), 3.31 (t, 2H), 6.94 (m, 2H), 7.09 (m, 2H), 7.15 (q, 1H), 7.32 (t, 1H), 7.39 (d, 1H), 7.80 (dd, 1H), 8.54 (dd, 1H), 10.5-11.5 (very br, 1H).

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate concentrated in vacuo to a yellow oil
  3. dissolutionThe crude intermediate oil was dissolved in 1 mL TFA
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customto provide the crude product as a dark oil
  6. customThe dark oil was purified by reversed phase preparative LC on a Gilson apparatus

Sources & evidence

ORD record
ord-c970b8450f19413f93c9a115cb5e77ce
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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