Potassium Carbonate → HCID 68966236, compound

HRID 2116136Notes

Reaction equation

HRID 2116136 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21](Br)[C:15]=3[O:14]2)(=O)=O)=CC=1.[CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B1OC(C)(C)C(C)(C)O1)([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(OCC2CC3C=CC=C(C4C=CC=CC=4C(C)C)C=3O2)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[N-:88]=[N+]=[N-].[Na+].N(CC1CC2C=CC=C(C3C=CC=CC=3C(C)C)C=2O1)=[N+]=[N-].[N-]=[N+]=[N-]>[Pd].CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:21]1[C:15]2[O:14][CH:13]([CH2:12][NH2:88])[CH2:17][C:16]=2[CH:18]=[CH:19][CH:20]=1)([CH3:25])[CH3:24]

Participants

11

Reactant 8

HCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 33558AzideHCID 85570p-ToluenesulfonateHCID 58747572(7-Bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 689670744,4,5,5-Tetramethyl-2-[2-(propan-2-yl)phenyl]-1,3,2-dioxaborolane2×HCID 86599205HCID 86599205, compoundHCID 86599206HCID 86599206, compound

Product 1

HCID 68966236HCID 68966236, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178424406HCID 178424406, compoundCatalyst

Procedure

Treatment of (±)-(7-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (4.81 g, 12.56 mmol) with 2-(2-isopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.63 g, 18.84 mmol, Intermediate 35), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.493 g, 0.627 mmol), and potassium carbonate (4.34 g, 31.38 mmol) generally according to the procedure described for Intermediate 37 provided (±)-[7-(2-isopropylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate. Treatment of the tosylate with sodium azide (2.10 g, 32.37 mmol) generally according to the procedure described for Intermediate 98 provided (±)-2-(azidomethyl)-7-(2-isopropylphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.22 g, 10 wt. %) generally according to the procedure described for Example 1 provided 2.15 g (56%) of (±)-[7-(2-isopropylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylamine as a white solid, hydrochloride salt. mp 202-204° C.; Anal. calcd. for C18H21NOHCl: C, 71.16; H, 7.30; N, 4.61. Found: C, 70.83; H, 7.34; N, 4.48.

Sources & evidence

ORD record
ord-f08e46d0c4444aa1aae66de92722a543
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…