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

HRID 2116168Notes

Reaction equation

HRID 2116168 reaction equation
[CH3:1]C1C=CC(S(OCC2CC3C=C(F)C=C(C4C=CC=CC=4F)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:34]([CH2:37][CH:38]1[CH2:42][C:41]2[CH:43]=[C:44]([F:54])[CH:45]=[C:46]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3F)[C:40]=2[O:39]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[F:54][C:44]1[CH:45]=[C:46]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[CH3:1])[C:40]2[O:39][CH:38]([CH2:37][NH2:34])[CH2:42][C:41]=2[CH:43]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599117(+/-)-[5-Fluoro-7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateHCID 86599227(+/-)-2-(Azidomethyl)-5-fluoro-7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran

Product 1

HCID 11960951(+/-)-1-[5-Fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamineYield 77%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-[5-fluoro-7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.84 g, 4.42 mmol) with sodium azide (1.15 g, 17.67 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-5-fluoro-7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.111 g, 10 wt. %) generally according to the procedure described for Example 1 provided 1.02 g (77%) of (±)-1-[5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 240-247° C. (dec); Anal. calcd. for C15H13F2NOHCl: C, 60.51; H, 4.74; N, 4.7. Found: C, 60.33; H, 4.69; N, 4.4.

Sources & evidence

ORD record
ord-cd36a1b7689b4a1bbde95c7f89c63ff9
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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