Sodium Azide → (+/-)-1-(5-Fluoro-7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine

HRID 2116165Notes

Reaction equation

HRID 2116165 reaction equation
CC1C=CC(S(OCC2CC3C=C(F)C=C(C4C=CC=CC=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:33]([CH2:36][CH:37]1[CH2:41][C:40]2[CH:42]=[C:43]([F:52])[CH:44]=[C:45]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:39]=2[O:38]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[F:52][C:43]1[CH:44]=[C:45]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:39]2[O:38][CH:37]([CH2:36][NH2:33])[CH2:41][C:40]=2[CH:42]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599114(+/-)-(5-Fluoro-7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 86599225(+/-)-2-(Azidomethyl)-5-fluoro-7-phenyl-2,3-dihydro-1-benzofuran

Product 1

HCID 11960950(+/-)-1-(5-Fluoro-7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamineYield 68%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-(5-fluoro-7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.50 g, 3.76 mmol) with sodium azide (0.979 g, 15.06 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-5-fluoro-7-phenyl-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.101 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.719 g (68%) of (±)-1-(5-fluoro-7-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine as a white solid, hydrochloride salt. mp 255-260° C.; Anal. calcd. for C15H14FNOHCl: C, 64.4; H, 5.4; N, 5.01. Found: C, 64.16; H, 5.54; N, 4.73.

Sources & evidence

ORD record
ord-96923c16df514038aadf0d42e9aa8a46
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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