HCID 66767215, compound → HCID 66767283, compound

HRID 1662009Notes

Reaction equation

HRID 1662009 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:15]=[N:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:18]=1)[N:10]([CH3:26])[N:9]=[CH:8]2>[Pd].C1COCC1>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][C:13]=2[C:14]2[CH:15]=[N:16][N:17]([C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[CH:18]=2)[N:10]([CH3:26])[N:9]=[CH:8]3)=[C:2]([F:1])[CH:30]=1

Participants

4

Reactant 1

HCID 66767215HCID 66767215, compound

Product 1

HCID 66767283HCID 66767283, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a 3 gallon tank is added tert-butyl 4-(5-(2-fluoro-4-nitrophenoxy)-1-methyl-1H-indazol-6-yl)-1H-pyrazole-1-carboxylate (433.0 g, 952.8 mmol) followed by THF (6.5 L) and Pd/C (21.65 g, 10% Pd/C and 21.65 g, 5% Pd/C). The mixture is heated to 35° C. under hydrogen gas for 2 hours. The reaction is then cooled to RT and allowed to stir under hydrogen gas overnight, then is heated to 40° C. under hydrogen gas for seven hours. An additional 2 g Pd/C (1 g, 10% Pd/C and 1 g, 5% Pd/C) is added and stirred under hydrogen gas for another hour and cooled to RT. The mixture is again stirred under hydrogen gas overnight and the reaction is completed. The mixture is filtered over a combination of GFF® and Watman® paper. The filtrate is concentrated to a slightly yellow solid (446 g, 110% recovery).

Workup

  1. temperatureThe reaction is then cooled to RT
  2. temperatureis heated to 40° C. under hydrogen gas for seven hours
  3. stirringstirred under hydrogen gas for another hour
  4. temperaturecooled to RT
  5. stirringThe mixture is again stirred under hydrogen gas overnight
  6. filtrationThe mixture is filtered over a combination of GFF® and Watman® paper
  7. concentrationThe filtrate is concentrated to a slightly yellow solid (446 g, 110% recovery)

Sources & evidence

ORD record
ord-c1885dbb86ba41cdb871fc94f04cd52a
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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