tert-butyl 4-(3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate → tert-butyl 4-(3-(5-amino-2-(2,4-difluorophenoxy)phenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)piperidine-1-carboxylate

HRID 633602Notes

Reaction equation

HRID 633602 reaction equation
[F:1][C:2]1[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]1[C:22]2[C:17](=[C:18]([O:36][CH3:37])[N:19]=[C:20]([C:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:24]=3)[CH:21]=2)[N:16]([CH3:38])[CH:15]=1.[H][H]>[Pd].FC(F)C(F)(F)O>[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:3]2[CH:39]=[CH:40][C:41]([F:43])=[CH:42][C:2]=2[F:1])=[C:6]([C:14]2[C:22]3[C:17](=[C:18]([O:36][CH3:37])[N:19]=[C:20]([CH:23]4[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH2:25][CH2:24]4)[CH:21]=3)[N:16]([CH3:38])[CH:15]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 90416432tert-butyl 4-(3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 90416106tert-butyl 4-(3-(5-amino-2-(2,4-difluorophenoxy)phenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)piperidine-1-carboxylateYield 107.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 145293621,1,2,2-Tetrafluoroethan-1-olSolvent

Procedure

A mixture of Example 183A (200 mg, 0.338 mmol), tetrafluoroethanol (20 mL), and 5% Pd/C (45 mg, 0.188 mmol) in a 50 mL pressure bottle was stirred at ambient temperature for 16 hours under 30 psi of hydrogen and at ambient temperature. The mixture was filtered through a nylon membrane. The filtrate was concentrated to give the title compound (205 mg, 0.363 mmol, 101% yield), which was used without further purification.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-cae1cbdda8f14841b6a0497ee15d3bd5
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

Loading…