2-Cyclopenten-1-one → 3-(2-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyridin-3-YL)cyclopent-2-enone

HRID 1880165Notes

Reaction equation

Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:25]1(=[O:30])[CH2:29][CH2:28][CH:27]=[CH:26]1.CN(C1CCCCC1)C1CCCCC1>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[S:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[NH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[C:2]([C:27]3[CH2:28][CH2:29][C:25](=[O:30])[CH:26]=3)=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of N-(4-(3-bromopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine (600 mg, 1.506 mmol), 2-cyclopenten-1-one (0.609 mL, 7.53 mmol), n-methyldicyclohexylamine (0.959 mL, 4.52 mmol) and bis(tri-tert-butylphosphine)palladium (0) (77 mg, 0.151 mmol) in Dioxane (4 mL) was capped, degassed and backfilled with argon. The reaction was heated to 90° C. After 6 h, the reaction was heated to 110° C. After 36 h, the reaction was cooled to 23° C., diluted with EtOAc (150 mL) and washed with water (100 mL) and brine (100 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 0.5-3% methanol/dichloromethane), affording the product as a yellow solid. MS (ESI, pos. ion) m/z: 400.1 (M+1).

Workup

customdegassed
temperaturethe reaction was heated to 110° C
waitAfter 36 h
temperaturethe reaction was cooled to 23° C.
additiondiluted with EtOAc (150 mL)
washwashed with water (100 mL) and brine (100 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (eluant: 0.5-3% methanol/dichloromethane)

Sources & evidence

ORD record: ord-cbfc0db826d742eb8a537d1203cba941
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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