Potassium Carbonate → (+/-)-2-(Azidomethyl)-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran

HRID 2116132Notes

Reaction equation

HRID 2116132 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(Br)C=3O2)(=O)=O)=CC=1.COC1C=CC=CC=1B(O)O.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:51][CH:52]2[CH2:56][C:55]3[CH:57]=[CH:58][CH:59]=[C:60]([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=4[O:67][CH3:68])[C:54]=3[O:53]2)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[N-:80]=[N+:81]=[N-:82].[Na+]>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[N:80]([CH2:51][CH:52]1[CH2:56][C:55]2[CH:57]=[CH:58][CH:59]=[C:60]([C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=3[O:67][CH3:68])[C:54]=2[O:53]1)=[N+:81]=[N-:82]

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 85570p-ToluenesulfonateHCID 27339582-Methoxyphenylboronic acidHCID 58747572(7-Bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 86599090(+)-[7-(2-Methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 86599203(+/-)-2-(Azidomethyl)-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 178424406HCID 178424406, compoundCatalyst

Procedure

Treatment of (±)-(7-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (5.0 g, 13.05 mmol) with 2-methoxyphenylboronic acid (2.57 g, 16.96 mmol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.532 g, 0.677 mmol), and potassium carbonate (4.51 g, 32.62 mmol) generally according to the procedure described for Intermediate 37 provided (±)-[7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate. Treatment of the tosylate with sodium azide (0.76 g, 11.69 mmol) generally according to the procedure described for Intermediate 98 gave (±)-2-(azidomethyl)-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.072 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.453 g (12%) of (±)-1-[7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp >250° C.; Anal. calcd. for C16H17NO2HCl: C, 65.86; H, 6.22; N, 4.8. Found: C, 65.72; H, 6.15; N, 4.86.

Sources & evidence

ORD record
ord-efaf8f39ab6643958ee87ad2af1ffe6f
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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