Aniline → HCID 50991079, compound

HRID 1360320Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][N:10]([S:12]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(=[O:14])=[O:13])[C:9]2[CH:24]=[C:25](Br)[CH:26]=[CH:27][C:8]=2[O:7]1)=[O:5])[CH3:2].[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N12CCCN=C1CCCCC2.[O:47]1CCC[CH2:48]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][N:10]([S:12]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(=[O:14])=[O:13])[C:9]2[CH:24]=[C:25]([C:48](=[O:47])[NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:26]=[CH:27][C:8]=2[O:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 6-bromo-4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester (200 mg, 0.408 mmol), molybdenum hexacarbonyl (108 mg, 0.408 mmol), aniline (114 mg, 1.22 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (192 mg, 1.22 mmol) trans-bis(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) (12 mg, 37 μmol), and tris(tert-butyl)phosphine tetrafluoroborate (6 mg, 20 μmol) in tetrahydrofuran (1 mL) was heated for 10 min at 140° C. under microwave irradiation, then the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient produced the title compound (111 mg, 51%). Off-white foam, MS (ISP)=531.0 (M+H)+.

Workup

customthe reaction mixture was partitioned between water and ethyl acetate
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-1d04441d3e0043fdae519dcd5cdb3783
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879845B2

Reaction notes

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