Sodium Azide → HCID 68963792, compound

HRID 2116123Notes

Reaction equation

HRID 2116123 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.[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH:32]=[C:31]1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1C=CC(S(OCC2CC3C=CC=C(C4OC5C=CC=CC=5C=4)C=3O2)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[N-:91]=[N+]=[N-].[Na+].N(CC1CC2C=CC=C(C3OC4C=CC=CC=4C=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>[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH:32]=[C:31]1[C:21]1[C:15]2[O:14][CH:13]([CH2:12][NH2:91])[CH2:17][C:16]=2[CH:18]=[CH:19][CH:20]=1

Participants

11

Reactant 8

HCID 33557Sodium AzideHCID 33558AzideHCID 62657Potassium Phosphate, TribasicHCID 85570p-ToluenesulfonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 86599077(+/-)-(7-{[(Trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 86599195HCID 86599195, compoundHCID 86599196HCID 86599196, compound

Product 1

HCID 68963792HCID 68963792, compoundYield 34.3%

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 2-benzofuranboronic acid (0.81 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 (±)-2′,3′-dihydro-2,7′-bi-1-benzofuran-2′-ylmethyl 4-methylbenzenesulfonate. Treatment of the tosylate with sodium azide (0.09 g, 1.32 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-2′-(azidomethyl)-2′,3′-dihydro-2,7′-bi-1-benzofuran. Treatment of the azide with palladium on carbon (0.03 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.12 g (12%) of (±)-1-(2′,3′-dihydro-2,7′-bi-1-benzofuran-2′-yl)methanamine as a white solid, hydrochloride salt. mp >220° C. (dec); Anal. calcd. for C19H17NOHCl.1.0H2O: C, 63.85; H, 5.67; N, 4.38. Found: C, 63.54; H, 5.1; N, 4.3.

Sources & evidence

ORD record
ord-27e8d113a2434fec9048ae86e0d23dfc
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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