Potassium Phosphate, Tribasic → HCID 89815032, compound

HRID 2172327Notes

Reaction equation

HRID 2172327 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH2:11][CH2:12][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]3)O1.Br[C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][C:29]=1[N:38]1[C:42]([CH3:43])=[CH:41][N:40]=[CH:39]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CCOC(C)=O>[CH3:43][C:42]1[N:38]([C:29]2[CH:30]=[C:31]([C:34]([F:37])([F:35])[F:36])[CH:32]=[CH:33][C:28]=2[C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH2:11][CH2:12][N:13]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:14]3)[CH:39]=[N:40][CH:41]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 57505885tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 89815318HCID 89815318, compound

Product 1

HCID 89815032HCID 89815032, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, Mo., 0.165 g, 0.233 mmol), tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (ASW Medchem, Brunswick, N.J., 1.254 g, 3.49 mmol), 1-(2-bromo-5-(trifluoromethyl)phenyl)-5-methyl-1H-imidazole (derived above, 0.710 g, 2.327 mmol), and potassium phosphate (1.976 g, 9.31 mmol) in 10 mL dioxane 5 mL water was heated to 120° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc and the organics were concentrated. The resulting residue was purified by silica gel column chromatography (0 to 100% EtOAc/heptane) yielding tert-butyl 5-(2-(5-methyl-1H-imidazol-1-yl)-4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.450 g, 0.984 mmol).

Workup

  1. concentrationthe organics were concentrated
  2. customThe resulting residue was purified by silica gel column chromatography (0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-438d42a6a5af445db0413fd6ab420e6e
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

Loading…