HCID 66767043, compound → HCID 86638474, compound

HRID 2195508Notes

Reaction equation

HRID 2195508 reaction equation
[F:1][C:2]1[CH:31]=[C:30]([N+:32]([O-])=O)[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:10]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[N:9]=[CH:8]2>CCOC(C)=O.[Pd]>[NH2:32][C:30]1[CH:29]=[CH:28][C:3]([O:4][C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][C:13]=2[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[N:10]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[N:9]=[CH:8]3)=[C:2]([F:1])[CH:31]=1

Participants

4

Reactant 1

HCID 66767043HCID 66767043, compound

Product 1

HCID 86638474HCID 86638474, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-(2-fluoro-4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ylcarbamate (400 mg, 0.85 mmol) in EtOAc (50 mL) is added Pd/C (10%, 50 mg). The resulting mixture is degassed by evacuation and backfilled with H2 three times. The mixture is stirred under an atmosphere of H2 at RT overnight. The solid is removed by filtration and the filtrate is concentrated. The residue is purified by silica gel column chromatography eluting with DCM:MeOH (10:1) to give the desired product (300 mg, 80% yield). MS (m/z): 443.2 (M+H).

Workup

  1. customThe resulting mixture is degassed by evacuation
  2. customThe solid is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by silica gel column chromatography
  5. washeluting with DCM:MeOH (10:1)

Sources & evidence

ORD record
ord-954beba321194747931be384ccdf0ce8
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

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