Sodium Azide → [4-(4-Methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide
Reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[C:18](Br)=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:23]=[N+:24]=[N-:25].[Na+]>>[CH3:17][C:16]1[CH:18]=[CH:19][C:20]([C:18]2[C:16]3[CH2:17][CH:13]([CH2:12][N:23]=[N+:24]=[N-:25])[O:14][C:15]=3[CH:21]=[CH:20][CH:19]=2)=[CH:21][CH:15]=1Participants
Procedure
Treatment of (±)-(4-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (5.0 g, 13.0 mmol), o-tolylboronic acid (2.66 g, 19.57 mmol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.512 g, 0.651 mmol), and potassium carbonate (4.51 g, 32.63 mmol) generally according to the procedure described for Intermediate 37 provided 4.0 g (77%) of (±)-1-[4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a yellow oil. Treatment of (±)-(4-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (3.8 g, 9.63 mmol) with sodium azide (2.5 g, 38.53 mmol) generally according to the procedure described for Intermediate 98 gave 2.39 g (94%) of [4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl azide. Treatment of the azide with palladium on carbon (0.239 g, 10 wt. %) generally according to the procedure described for Example 1 provided 2.3 g (93%) of (±)-1-[4-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 239-241° C.; Anal. calcd. for C16H17NOHCl: C, 69.69; H, 6.58; N, 5.08. Found: C, 69:36; H, 6.64; N, 4.93.
Sources & evidence
- ORD record
- ord-bef61dcb94684fdb845888fddd9f8ac5
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435837B2
Reaction notes
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