HCID 90409320, compound → HCID 90205451, compound

HRID 869129Notes

Reaction equation

HRID 869129 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[O:10][CH:11]1[CH2:14][O:13][CH2:12]1)([O-])=O>CO.[Pd]>[O:13]1[CH2:12][CH:11]([O:10][C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[NH2:1])[CH2:14]1

Participants

4

Reactant 1

HCID 90409320HCID 90409320, compound

Product 1

HCID 90205451HCID 90205451, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Nitro-4-(oxetan-3-yloxy)pyridine (499 mg) was dissolved in methanol (10 mL) and Pd on C, wet, Degussa was added. The reaction mixture was flushed nitrogen twice and then stirred under a hydrogen atmosphere for 3 hours. The reaction mixture was filtered through a prewetted (methanol, 5 mL) Celite cartridge (2.5 g) and washed with methanol (25 mL). The filtrate was concentrated in vacuo to afford the desired product as a pale orange oil (432 mg, 97.7%). LC-MS (M+H)+ 196.3; 1H NMR (500 MHz, DMSO-d6) δ 7.91 (s, 1H), 7.67 (d, J=5.3 Hz, 1H), 6.45 (d, J=5.3 Hz, 1H), 5.32 (tt, J=6.0, 4.8 Hz, 1H), 4.96 (s, 2H), 4.95 (ddd, J=7.1, 6.0, 1.0 Hz, 2H), 4.59 (ddd, J=7.3, 4.8, 1.0 Hz, 2H).

Workup

  1. customThe reaction mixture was flushed nitrogen twice
  2. filtrationThe reaction mixture was filtered through
  3. washwashed with methanol (25 mL)
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7c640b02ddce4058b3c46acf16bd3ed7
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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