Potassium Carbonate → HCID 11960947, compound

HRID 2116161Notes

Reaction equation

HRID 2116161 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([Cl:30])[CH:20]=[C:21](OS(C(F)(F)F)(=O)=O)[C:15]=3[O:14]2)(=O)=O)=CC=1.[CH3:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C(C1C=CC=CC=1B1OC(C)(C)C(C)(C)O1)(C)C.CC1C=CC(S(OCC2CC3C=C(Cl)C=C(C4C=CC=CC=4C)C=3O2)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[N-:105]=[N+]=[N-].[Na+].N(CC1CC2C=C(Cl)C=C(C3C=CC=CC=3C)C=2O1)=[N+]=[N-].[N-]=[N+]=[N-]>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].[Pt]>[Cl:30][C:19]1[CH:20]=[C:21]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[CH3:31])[C:15]2[O:14][CH:13]([CH2:12][NH2:105])[CH2:17][C:16]=2[CH:18]=1

Participants

12

Reactant 9

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 33558AzideHCID 85570p-ToluenesulfonateHCID 27332672-Methylphenyl boronic acidHCID 689670744,4,5,5-Tetramethyl-2-[2-(propan-2-yl)phenyl]-1,3,2-dioxaborolaneHCID 86599104HCID 86599104, compoundHCID 86599217HCID 86599217, compoundHCID 86599221HCID 86599221, compound

Product 1

HCID 11960947HCID 11960947, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 53485975CID 53485975Catalyst

Procedure

Treatment of (±)-(5-chloro-7-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.37 g, 2.81 mmol) with 2-methylphenylboronic acid (0.65 g, 4.60 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.25 g, 0.30 mmol), and potassium carbonate (0.83 g, 6.0 mmol) generally according to the procedure described for Intermediate 35 provided (±)-[5-chloro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate. Treatment of the tosylate with sodium azide (1.04 g, 16.1 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-5-chloro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (200 mg, 5 wt. %) generally according to the procedure described for Example 1 gave 0.70 g (80%) of (±)-1-[5-chloro-7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a light yellow solid, hydrochloric salt. mp 160-163° C.; Anal. calcd. for C16H16ClNOHCl: C, 61.95; H, 5.52; N, 4.52. Found: C, 57.75; H, 5.4; N, 3.95.

Sources & evidence

ORD record
ord-b9bbb09e3a454431b4ecf0759122abd4
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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