HCID 86599232, compound → HCID 15942449, compound

HRID 2116176Notes

Reaction equation

HRID 2116176 reaction equation
[N:1]([CH2:4][C:5]1([CH3:20])[CH2:9][C:8]2[CH:10]=[C:11]([Cl:19])[CH:12]=[C:13]([C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)[C:7]=2[O:6]1)=[N+]=[N-]>[Pt]>[Cl:19][C:11]1[CH:12]=[C:13]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[C:7]2[O:6][C:5]([CH2:4][NH2:1])([CH3:20])[CH2:9][C:8]=2[CH:10]=1

Participants

3

Reactant 1

HCID 86599232HCID 86599232, compound

Product 1

HCID 15942449HCID 15942449, compound

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

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-d60065e26e33465dbc2ab1fe0293af17
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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