Sodium Azide → HCID 11960770, compound

HRID 2116137Notes

Reaction equation

HRID 2116137 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(C4C=CC=C(F)C=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:33]([CH2:36][CH:37]1[CH2:41][C:40]2[CH:42]=[CH:43][CH:44]=[C:45]([C:46]3[CH:51]=[CH:50][CH:49]=[C:48]([F:52])[CH:47]=3)[C:39]=2[O:38]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[F:52][C:48]1[CH:47]=[C:46]([C:45]2[C:39]3[O:38][CH:37]([CH2:36][NH2:33])[CH2:41][C:40]=3[CH:42]=[CH:43][CH:44]=2)[CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599093HCID 86599093, compoundHCID 86599207HCID 86599207, compound

Product 1

HCID 11960770HCID 11960770, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-[7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.68 g, 4.22 mmol) with sodium azide (1.09 g, 16.88 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.107 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.95 g (81%) of (±)-1-[7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 200-202° C., Anal. calcd. for C15H14FNOHCl: C, 64.4; H, 5.4; N, 5.01. Found: C, 63.93; H, 5.48; N, 4.73.

Sources & evidence

ORD record
ord-79033e0122b0441a8ecc2bea366d56db
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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