Sodium Azide → HCID 68964821, compound

HRID 2116107Notes

Reaction equation

HRID 2116107 reaction equation
CC1C=CC(S(OCC2CC3C(C(F)(F)F)=CC=C(Cl)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[N:31]([CH2:34][CH:35]1[CH2:39][C:38]2[C:40]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:42]=[C:43]([Cl:44])[C:37]=2[O:36]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[Cl:44][C:43]1[C:37]2[O:36][CH:35]([CH2:34][NH2:31])[CH2:39][C:38]=2[C:40]([C:45]([F:48])([F:46])[F:47])=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 86599066HCID 86599066, compoundHCID 86599180HCID 86599180, compound

Product 1

HCID 68964821HCID 68964821, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-[7-chloro-4-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.0 g, 2.46 mmol) with sodium azide (0.64 g, 9.83 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-7-chloro-4-(trifluoromethyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.060 g, 10 wt. %) generally according to the procedure described for Example 1 afforded 0.350 g (64%) of (±)-1-[7-chloro-4-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp >250° C.; Anal. calcd. for C10H9F3ClNOHCl: C, 41.69; H, 3.5; N, 4.86. Found: C, 41.78; H, 3.43; N, 4.77.

Sources & evidence

ORD record
ord-b46bb8732b0e48d8aa57b54891165099
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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