Triphenylphosphine → HCID 11960953, compound

HRID 2116169Notes

Reaction equation

[N-]=[N+]=[N-].[Na+].[N:5]([CH2:8][CH:9]1[CH2:13][C:12]2[CH:14]=[C:15]([F:28])[CH:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[C:11]=2[O:10]1)=[N+]=[N-].[N-]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[F:28][C:15]1[CH:16]=[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([F:27])([F:25])[F:26])[C:11]2[O:10][CH:9]([CH2:8][NH2:5])[CH2:13][C:12]=2[CH:14]=1

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 33557Sodium Azide

HCID 33558Azide

HCID 86599228HCID 86599228, compound

Product 1

HCID 11960953HCID 11960953, compoundYield 89%

Procedure

Treatment of (±)-{5-fluoro-7-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl)}methyl 4-methylbenzenesulfonate (5.34 g, 0.011 mol) with sodium azide (2.60 g, 0.04 mol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-5-fluoro-7-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran. Treatment of the azide with triphenylphosphine (2.89 g, 0.011 mol) generally according to the procedure described for Example 21 afforded 3.25 g (89%) of (±)-1-{5-fluoro-7-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methanamine as a white solid, hydrochloride salt. mp 196-198° C. (dec); Anal. calcd. for C16H13F4NOHCl: C, 55.26; H, 4.06; N, 4.03. Found: C, 55.88; H, 4.26; N, 3.77.

Sources & evidence

ORD record: ord-b290ffcac9c44302a5ac11785722431b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

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