(+/-)-2-(Azidomethyl)-5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran → (+/-)-1-[5-Fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
Reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][C:8]2[CH:10]=[C:11]([F:21])[CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[C:7]=2[O:6]1)=[N+]=[N-]>[Pd]>[F:21][C:11]1[CH:12]=[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[C:7]2[O:6][CH:5]([CH2:4][NH2:1])[CH2:9][C:8]=2[CH:10]=1Participants
3
Procedure
Treatment of (±)-[5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.48 g, 3.59 mmol) with sodium azide (0.933 g, 14.35 mmol) generally according to the procedure described for Intermediate 98 gave (±)-2-(azidomethyl)-5-fluoro-7-(2-methylphenyl)-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 0.555 g (53%) of (±)-1-[5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 229-234° C.; Anal. calcd. for C16H16FNOHCl.0.1H2O: C, 65.02; H, 5.87; N, 4.74. Found: C, 64.99; H, 5.83; N, 4
Sources & evidence
- ORD record
- ord-305c3d5475634544a4312ec6f40f13a1
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435837B2
Reaction notes
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