Sodium Azide → HCID 68961529, compound

HRID 2116178Notes

Reaction equation

HRID 2116178 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[N-]=[N+]=[N-].[Na+].[N:16]([CH2:19][C:20]1([CH3:35])[CH2:24][C:23]2[CH:25]=[C:26]([Cl:34])[CH:27]=[C:28]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)[C:22]=2[O:21]1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pt]>[Cl:34][C:26]1[CH:27]=[C:28]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[O:21][C:20]([CH2:19][NH2:16])([CH3:35])[CH2:24][C:23]=2[CH:25]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 33558AzideHCID 85570p-ToluenesulfonateHCID 86599235HCID 86599235, compound

Product 1

HCID 68961529HCID 68961529, 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 (2.90 g, 5.8 mmol), thiophene-2-boronic acid (1.11 g, 8.7 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.47 g, 0.58 mmol), and potassium carbonate (1.6 g, 11.6 mmol) generally according to the procedure described for Intermediate 35 gave (±)-(5-chloro-2-methyl-7-thien-2-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 provided (±)-2-(azidomethyl)-5-chloro-2-methyl-7-thien-2-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 0.58 g of (±)-(5-chloro-2-methyl-7-thien-2-yl-2,3-dihydro-1-benzofuran-2-yl)methylamine as a white solid, hydrochloride salt. mp 251-252° C.; Anal. calcd. for C14H14ClNOSHCl: C, 53.17; H, 4.78; N, 4.43. Found: C, 51.17; H, 4.48; N, 4.32.

Sources & evidence

ORD record
ord-f5aef73b50c4437896aaebb03f047976
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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