(+/-)-2-(Azidomethyl)-7-(3-chloro-4-fluorophenyl)-2,3-dihydro-1-benzofuran → (+/-)-1-[7-(3-Chloro-4-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine
Reaction equation
[N:1]([CH2:4][CH:5]1[CH2:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=3)[C:7]=2[O:6]1)=[N+]=[N-]>[Pd]>[Cl:21][C:16]1[CH:15]=[C:14]([C:13]2[C:7]3[O:6][CH:5]([CH2:4][NH2:1])[CH2:9][C:8]=3[CH:10]=[CH:11][CH:12]=2)[CH:19]=[CH:18][C:17]=1[F:20]Participants
3
Procedure
Treatment of (±)-[7-(3-chloro-4-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (0.68 g, 1.57 mmol) with sodium azide (0.25 g, 3.92 mmol) generally according to the procedure described for Intermediate 98 gave (±)-2-(azidomethyl)-7-(3-chloro-4-fluorophenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.035 g, 10 wt. %) generally according to the procedure described for Example 1 afforded 0.186 g (38%) of (±)-1-[7-(3-chloro-4-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp >210° C.; Anal. calcd. for C15H13ClFNOHCl: C, 57.34; H, 4.49; N, 4.46. Found: C, 57.38; H, 4.32; N, 4.55.
Sources & evidence
- ORD record
- ord-58943ea2ecf24be1be43e999595d01a0
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435837B2
Reaction notes
Loading…