Sodium Azide → HCID 11947798, compound

HRID 2116116Notes

Reaction equation

HRID 2116116 reaction equation
[N-]=[N+]=[N-].[Na+].[N:5]([CH2:8][CH:9]1[CH2:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=3)[C:11]=2[O:10]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd]>[F:26][C:24]([F:25])([F:27])[C:22]1[CH:23]=[C:18]([C:17]2[C:11]3[O:10][CH:9]([CH2:8][NH2:5])[CH2:13][C:12]=3[CH:14]=[CH:15][CH:16]=2)[CH:19]=[C:20]([C:28]([F:29])([F:30])[F:31])[CH:21]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 33558AzideHCID 86599188HCID 86599188, compound

Product 1

HCID 11947798HCID 11947798, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of {7-[3,5-bis(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl methyl 4-methylbenzenesulfonate (0.75 g, 1.45 mmol) with sodium azide (0.24 g, 3.62 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-7-[3,5-bis(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (10%, 0.075 g) generally according to the procedure described for Example 1 afforded 0.270 g (47%) of (±)-1-{7-[3,5-bis(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methanamine as a white solid, hydrochloride salt. mp 174-175° C. (dec.); Anal. calcd. for C17H13F6NOHCl: C, 51.34; H, 3.55; N, 3.52. Found: C, 51.25; H, 3.57; N, 3.68.

Sources & evidence

ORD record
ord-7824458bc4f34dcdb411a5739eaad82e
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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