Sodium Azide → (+/-)-2-(Azidomethyl)-5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran

HRID 2116166Notes

Reaction equation

HRID 2116166 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([F:29])[CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[CH3:28])[C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:30]=[N+:31]=[N-:32].[Na+]>>[N:30]([CH2:12][CH:13]1[CH2:17][C:16]2[CH:18]=[C:19]([F:29])[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[C:15]=2[O:14]1)=[N+:31]=[N-:32]

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 86599115(+/-)-[5-Fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 86599226(+/-)-2-(Azidomethyl)-5-fluoro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran

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-fcc5d7c59ee543699fdb2efd78413377
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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