Sodium Carbonate → HCID 68153598, compound

HRID 1946929Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2([CH3:16])[N:13]=[C:12]([O:14][CH3:15])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:17][C:18]1[CH:19]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:21]=[C:22]([Cl:24])[CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:17][C:18]1[CH:19]=[C:20]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3([CH3:16])[N:13]=[C:12]([O:14][CH3:15])[CH2:11][O:10][CH2:9]3)[CH:3]=2)[CH:21]=[C:22]([Cl:24])[CH:23]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A degassed solution of (RS)-3-(3-bromo-phenyl)-5-methoxy-3-methyl-3,6-dihydro-2H[1,4]oxazine (intermediate XI-1) (200 mg, 0.7 mmol) in 1,2-dimethoxyethane (3 ml) and 2-(3,5-dichloro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (288 mg, 1.1 mmol) was treated consecutively with a solution of sodium carbonate (2M, 0.6 ml), triphenylphosphine (38 mg, 0.1 mmol), and palladium(II)acetate (16 mg, 0.1 mmol). The mixture was heated overnight in a sealed tube at 105° C. For the workup, the reaction mixture was evaporated at reduced pressure and the residue directly purified by chromatography on a silica-amine phase using a gradient of heptane/ethylacetate=100/0 to 60/10 as the eluent. The (RS)-3-(3′,5′-dichloro-biphenyl-3-yl)-5-methoxy-3-methyl-3,6-dihydro-2H-[1,4]oxazine was obtained as a colorless oil (160 mg, 65% of theory). MS (ISP): m/z=350.2 [M+H]+.

Workup

customFor the workup, the reaction mixture was evaporated at reduced pressure
customthe residue directly purified by chromatography on a silica-amine phase

Sources & evidence

ORD record: ord-a4d0e99322d3462bbcddcf2517c4567b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399459B2

Reaction notes

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