Sodium Carbonate → 1-[7-Bromo-5-(5-methoxy-pyridin-3-yl)-benzothiazol-2-yl]-3-ethyl-urea

HRID 1941956Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([Br:17])[C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:24][O:25][C:26]1[CH:27]=[N:28][CH:29]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:31]=1>CN(C)C=O.O>[Br:17][C:4]1[C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=[C:2]([C:30]2[CH:29]=[N:28][CH:27]=[C:26]([O:25][CH3:24])[CH:31]=2)[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A stirred mixture of 1-(5,7-dibromo-benzothiazol-2-yl-3-ethyl urea (300 mg, 0.79 mmol), sodium carbonate (167 mg, 1.58 mmol), (1,1′-bis(diphenylphosphino)ferrocene)dichloro-palladium(II) (45 mg, 0.05 mmol), 3-methoxy-5-pyridineboronic acid pinacol ester (186 mg, 0.79 mmol) in dimethyl formamide (8 ml) and water (2 ml), was purged with nitrogen for 5 min and heated at 100° C. for 1 h. The reaction mixture was concentrated in vacuo then partitioned between ethyl acetate and water. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with 0 to 5% methanol in ethyl acetate to give 1-[7-Bromo-5-(5-methoxy-pyridin-3-yl)-benzothiazol-2-yl]-3-ethyl-urea 1 as a white solid (49 mg, 15%).

Workup

customwas purged with nitrogen for 5 min
concentrationThe reaction mixture was concentrated in vacuo
customthen partitioned between ethyl acetate and water
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by silica gel chromatography
washeluting with 0 to 5% methanol in ethyl acetate

Sources & evidence

ORD record: ord-6e5cbba2ebe34b07bc3a634aa09b01e3
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389516B2

Reaction notes

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