HCID 86599213, compound → HCID 11960867, compound

HRID 2116150Notes

Reaction equation

HRID 2116150 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]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[C:7]=2[O:6]1)=[N+]=[N-]>[Pd]>[F:22][C:20]([F:21])([F:23])[C:17]1[CH:16]=[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]=1

Participants

3

Reactant 1

HCID 86599213HCID 86599213, compound

Product 1

HCID 11960867HCID 11960867, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-{7-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methyl 4-methylbenzenesulfonate (3.3 g, 7.34 mmol) with sodium azide (1.91 g, 29.38 mmol) generally according to the procedure described for Intermediate 98 gave (±)-2-(azidomethyl)-7-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.205 g, 10 wt. %) generally according to the procedure described for Example 1 provided 1.82 g (75%) of (±)-1-{7-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl methanamine as a white solid, hydrochloride salt. mp >250° C.; Anal. calcd. for C16H14F3NOHCl: C, 58.28; H, 4.59; N, 4.25. Found: C, 57.47; H, 4.82; N, 3.65.

Sources & evidence

ORD record
ord-5258cbf4f01c4124a28b6a61cdeab3f1
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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