Sodium Carbonate → HCID 59327250, compound

HRID 1880059Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24](Br)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[O:26]1[CH2:31][CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH2:28][CH2:27]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:29]3[CH2:30][CH2:31][O:26][CH2:27][CH:28]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

Conditions

Temperature: 120 °C

Procedure

To a glass microwave vial was added benzo[d]thiazol-2-yl(4-(3-bromopyridin-2-yloxy)phenyl)methanone (1.0902 g, 2.65 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.114 g, 5.30 mmol), trans-dichlorobis(triphenylphosphine) palladium (II) (0.149 g, 0.212 mmol), and sodium carbonate (0.843 g, 7.95 mmol) in DMF (6.63 mL) and water (2.209 mL). The reaction mixture was stirred and heated in a Biotage Initiator microwave reactor at 120° C. for 20 min. Solvent was evaporated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (40S), eluting with a gradient of 5% to 50% EtOAc in hexane, to provide benzo[d]thiazol-2-yl(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone. MS (ESI, pos. ion) m/z: 414.8 (M+1).

Workup

customSolvent was evaporated
customchromatographed through a Biotage pre-packed silica gel column (40S)
washeluting with a gradient of 5% to 50% EtOAc in hexane

Sources & evidence

ORD record: ord-8b235ba7dd29453c9b8e406db759d883
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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