1,4-Dibromobutane → 2-(3-Methyl-4-(pyrrolidin-1-yl)isothiazol-5-yl)isoindoline-1,3-dione

HRID 1850700Notes

Reaction equation

CCN(C(C)C)C(C)C.Br[CH2:11][CH2:12][CH2:13][CH2:14]Br.[NH2:16][C:17]1[C:18]([CH3:35])=[N:19][S:20][C:21]=1[NH:22][C:23]([C:25]1[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=1[C:27](OC)=[O:28])=[O:24]>CN(C=O)C>[CH3:35][C:18]1[C:17]([N:16]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[C:21]([N:22]2[C:23](=[O:24])[C:25]3[C:26](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:27]2=[O:28])[S:20][N:19]=1

Participants

Conditions

Temperature: 130 °C

Procedure

DIEA (332.7 mg, 448.4 μL, 2.574 mmol), 1,4-dibromobutane (555.8 mg, 307.4 μL, 2.574 mmol) was added to a solution of methyl 2-[(4-amino-3-methyl-isothiazol-5-yl)carbamoyl]benzoate (150 mg, 0.5149 mmol) in DMF (4 mL) and the mixture was stirred at 130° C. for 40 min in a microwave. The reaction mixture was concentrated in vacuo to yield 2-(3-methyl-4-(pyrrolidin-1-yl)isothiazol-5-yl)isoindoline-1,3-dione that was used in next step without further purification. MS (ES+) 314.1.

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-791848be7ce342d7a1afa1cbcc578cbb
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957078B2

Reaction notes

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