4-Methoxy-2-(trifluoromethyl)aniline → Tert-butyl[3-fluoro-5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamate

HRID 1428210Notes

Reaction equation

HRID 1428210 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:17])[C:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:6][CH:7]=1.[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=1>>[C:12]([O:11][C:10](=[O:16])[NH:9][CH2:8][C:5]1[C:4]([F:17])=[CH:3][C:2]([NH:24][C:23]2[CH:25]=[CH:26][C:20]([O:19][CH3:18])=[CH:21][C:22]=2[C:27]([F:28])([F:29])[F:30])=[CH:7][N:6]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 226017214-Methoxy-2-(trifluoromethyl)anilineHCID 68451985Tert-butyl ((5-bromo-3-fluoropyridin-2-YL)methyl)carbamate

Product 1

HCID 68025880Tert-butyl[3-fluoro-5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridin-2-ylmethyl]-carbamateYield 26%

Procedure

Analogously to Example 1a), tert-butyl (5-bromo-3-fluoro-pyridin-2-ylmethyl)-carbamate (0.55 mmol) was reacted with 4-methoxy-2-trifluoromethyl-aniline. The crude product was purified by chromatography (column: Varian Pursuit XRS C18; 10 μM; 41.4×250 mm, gradient: acetonitrile/water/CF3COOH: 10/90/0.1→100/0/0.1). The product was thus obtained in a yield of 26% of theory.

Workup

  1. customThe crude product was purified by chromatography (column: Varian Pursuit XRS C18; 10 μM; 41.4×250 mm, gradient: acetonitrile/water/CF3COOH: 10/90/0.1→100/0/0.1)
  2. customThe product was thus obtained in a yield of 26% of theory

Sources & evidence

ORD record
ord-80b04ac597994e889fac3493aeb6144a
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

Loading…