Sodium Carbonate → N-(6-(5-(4-(1-hydroxyethyl)phenylsulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide

HRID 2077570Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([OH:20])[CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:29]2[CH:41]=[CH:40][C:32]3[N:33]=[C:34]([NH:36][C:37](=[O:39])[CH3:38])[S:35][C:31]=3[CH:30]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C(Cl)Cl.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:20][CH:18]([C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:4]2[CH:3]=[C:2]([C:29]3[CH:41]=[CH:40][C:32]4[N:33]=[C:34]([NH:36][C:37](=[O:39])[CH3:38])[S:35][C:31]=4[CH:30]=3)[CH:7]=[N:6][CH:5]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1)[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-(5-bromopyridin-3-yl)-4-(1-hydroxyethyl)benzenesulfonamide (0.120 g, 0.34 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.11 g, 0.34 mmol), tetrakis(triphenylphosphine)palladium (0.019 g, 0.017 mmol) in 1 ml of dioxane and 1 ml of aq. 2M sodium carbonate was heated under microwave (CEM) at 120 W, 100° C. for 20 min. Then, the resultant was diluted with DCM and water. The organic layer was separated, dried and concentrated. The residue was purified by HPLC (5-60% CH3CN in water gradient) to give a light yellow solid (25 mg, 16%). MS (ESI pos. ion) Found m/z: 469, (M+H)+.

Workup

customThe organic layer was separated
customdried
concentrationconcentrated
customThe residue was purified by HPLC (5-60% CH3CN in water gradient)

Sources & evidence

ORD record: ord-62d38f85dc864dff8f9543a158cf0093
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928140B2

Reaction notes

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