Potassium Carbonate → HCID 11960766, compound

HRID 2116130Notes

Reaction equation

HRID 2116130 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21](Br)[C:15]=3[O:14]2)(=O)=O)=CC=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(OCC2CC3C=CC=C(C4C=CC=CC=4C(F)(F)F)C=3O2)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[N-:84]=[N+]=[N-].[Na+].N(CC1CC2C=CC=C(C3C=CC=CC=3C(F)(F)F)C=2O1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd].CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:21]1[C:15]2[O:14][CH:13]([CH2:12][NH2:84])[CH2:17][C:16]=2[CH:18]=[CH:19][CH:20]=1

Participants

11

Reactant 8

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 33558AzideHCID 85570p-ToluenesulfonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 58747572(7-Bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 86599086HCID 86599086, compoundHCID 86599201HCID 86599201, compound

Product 1

HCID 11960766HCID 11960766, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178424406HCID 178424406, compoundCatalyst

Procedure

Treatment of (7-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (4.0 g, 10.44 mmol) with 2-(trifluoromethyl)phenylboronic acid (2.57 g, 13.6 mmol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.426 g, 0.542 mmol), and potassium carbonate (3.61 g, 26.09 mmol) generally according to the procedure described for Intermediate 37 provided (±)-{7-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methyl 4-methylbenzenesulfonate. Treatment of the tosylate with sodium azide (1.31 g, 20.25 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.160 g, 10 wt. %) generally according to the procedure described for Example 1 provided 1.05 g (65%) of (±)-1-{7-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methanamine as a white solid, hydrochloride salt. mp 204-205° C.; Anal. calcd. for C16H14F3NOHCl: C, 58.25; H, 4.59; N, 4.25. Found: C, 57.57; H, 4.52; N, 4.08.

Sources & evidence

ORD record
ord-b4bcfbb2d4b149889736591508ea67a1
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…