Potassium Carbonate → HCID 86599232, compound

HRID 2116175Notes

Reaction equation

HRID 2116175 reaction equation
CC1C=CC(S(OCC2(C)CC3C=C(Cl)C=C(OS(C(F)(F)F)(=O)=O)C=3O2)(=O)=O)=CC=1.S1C=CC(B(O)O)=C1.C(=O)([O-])[O-].[K+].[K+].C(C1C=CC=CC=1B1OC(C)(C)C(C)(C)O1)(C)C.CC1C=CC(S(O[CH2:75][C:76]2([CH3:91])[CH2:80][C:79]3[CH:81]=[C:82]([Cl:90])[CH:83]=[C:84]([C:85]4[CH:89]=[CH:88][S:87][CH:86]=4)[C:78]=3[O:77]2)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[N-:103]=[N+:104]=[N-:105].[Na+]>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]>[N:103]([CH2:75][C:76]1([CH3:91])[CH2:80][C:79]2[CH:81]=[C:82]([Cl:90])[CH:83]=[C:84]([C:85]3[CH:89]=[CH:88][S:87][CH:86]=3)[C:78]=2[O:77]1)=[N+:104]=[N-:105]

Participants

9

Reactant 7

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 85570p-ToluenesulfonateHCID 581760Thiophene-3-boronic acidHCID 689670744,4,5,5-Tetramethyl-2-[2-(propan-2-yl)phenyl]-1,3,2-dioxaborolaneHCID 86599127HCID 86599127, compoundHCID 86599233HCID 86599233, compound

Product 1

HCID 86599232HCID 86599232, compound

Reagents, catalysts & solvents 1

HCID 53485975CID 53485975Catalyst

Procedure

Treatment of (±)-(5-chloro-2-methyl-7-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (5.00 g, 10.0 mmol), thiophene-3-boronic acid (1.92 g, 15.0 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.82 g, 1.0 mmol), and potassium carbonate (2.76 g, 20.0 mmol) generally according to the procedure described for Intermediate 35 provided (±)-(5-chloro-2-methyl-7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate. Treatment of the tosylate with sodium azide (2.00 g, 30.7 mmol) generally according to the procedure described for Intermediate 98 gave (±)-2-(azidomethyl)-5-chloro-2-methyl-7-thien-3-yl-2,3-dihydro-1-benzofuran. Treatment of the azide with sulfided platinum on carbon (0.250 g, 5 wt. %) generally according to the procedure described for Example 1 afforded 0.7 g (22%0 of (±)-(5-chloro-2-methyl-7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methylamine as a white solid, hydrochloride salt. mp 295-298° C. (dec); Anal. calcd. for C14H14ClNOSHCl: C, 53.17; H, 4.78; N, 4.43. Found: C, 52.80; H, 4.74; N, 4.24.

Sources & evidence

ORD record
ord-2dd0bee92ac746fdb4de5245d0d84836
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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