Sodium Azide → HCID 68966176, compound

HRID 2116117Notes

Reaction equation

HRID 2116117 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21](OS(C(F)(F)F)(=O)=O)[C:15]=3[O:14]2)(=O)=O)=CC=1.[C:30]1(B(O)O)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1C=CC(S(OCC2CC3C=CC=C(C4C5C(=CC=CC=5)C=CC=4)C=3O2)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[N-:93]=[N+]=[N-].[Na+].N(CC1CC2C=CC=C(C3C4C(=CC=CC=4)C=CC=3)C=2O1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:30]1([C:21]2[C:15]3[O:14][CH:13]([CH2:12][NH2:93])[CH2:17][C:16]=3[CH:18]=[CH:19][CH:20]=2)[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1

Participants

11

Reactant 8

HCID 33557Sodium AzideHCID 33558AzideHCID 62657Potassium Phosphate, TribasicHCID 85570p-ToluenesulfonateHCID 2545321-Naphthaleneboronic acidHCID 86599077(+/-)-(7-{[(Trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 86599189HCID 86599189, compoundHCID 86599190HCID 86599190, compound

Product 1

HCID 68966176HCID 68966176, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

Treatment of (±)-(7-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.5 g, 3.32 mmol) with 1-naphthaleneboronic acid (0.86 g, 4.97 mmol), tetrakis(triphenylphosphine)palladium(0) (0.38 g, 0.33 mmol), and potassium phosphate (1.41 g, 6.63 mmol) generally according to the procedure described for Intermediate 50 provided (±)-[7-(1-naphthyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate. Treatment of the tosylate with sodium azide (0.10 g, 1.49 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2-(azidomethyl)-7-(1-naphthyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.03 g, 10 wt. %) generally according to the procedure described for Example 1 gave 0.10 g (10%) of (±)-1-[7-(1-naphthyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 120-124° C.; Anal. calcd. for C19H17NOHCl.0.5H2O: C, 71.13; H, 5.97; N, 4.37. Found: C, 70.93; H, 5.74; N, 4.58.

Sources & evidence

ORD record
ord-38bdc6111697477c97a009787e6c680f
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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