Potassium Carbonate → HCID 86599108, compound

HRID 2115989Notes

Reaction equation

HRID 2115989 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][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]=3O2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=C[CH:37]=1.[C:41](=[O:44])([O-])[O-].[K+].[K+]>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]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([Cl:30])[CH:20]=[C:21]([C:15]4[CH:35]=[CH:34][CH:33]=[C:32]([CH3:37])[CH:31]=4)[C:41]=3[O:44]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27339503-Tolylboronic acidHCID 86599104HCID 86599104, compound

Product 1

HCID 86599108HCID 86599108, compound

Reagents, catalysts & solvents 1

HCID 53485975CID 53485975Catalyst

Procedure

Treatment of (±)-(5-chloro-7-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.50 g, 3.10 mmol) with 3-methylphenylboronic acid (0.63 g, 4.60 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.252 g, 0.30 mmol), and potassium carbonate (0.829 g, 6.0 mmol) generally according to the procedure described for Intermediate 35 gave (±)-[5-chloro-7-(3-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate as a colorless oil. Treatment of the tosylate with sodium azide (0.31 g, 4.78 mmol) generally according to the procedure described for Intermediate 98 afforded 0.32 g (34%) of (±)-2-(azidomethyl)-5-chloro-7-(3-methylphenyl)-2,3-dihydro-1-benzofuran as a tan solid. mp 48-50° C.; Anal. calcd. for C16H14ClN3O: C, 64.11; H, 4.71; N, 14.02. Found: C, 62.95; H, 4.62; N, 13.72.

Sources & evidence

ORD record
ord-e53b4a78b1844572a79f3953aec2c16b
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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