Lithium Chloride → HCID 59397235, compound

HRID 2076361Notes

Reaction equation

[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:23]4[C:18]([CH2:25][CH2:26]F)([CH2:19][CH2:20][C:21](=[O:24])[CH:22]=4)[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+]>CN(C)C=O>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:23]4[C:18]5([CH2:19][CH:20]([C:21](=[O:24])[CH:22]=4)[CH2:26][CH2:25]5)[CH2:17][C:14]=32)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 2-benzyl-9a-(2-fluoroethyl)-8,9,9a,10-tetrahydroindeno[2,1-e]indazol-7(2H)-one (1.0 g, 2.5 mmol) in 25 mL, of dimethylformamide was added lithium chloride (1.05 g, 25 mmol) and the stirred mixture was heated to 150° C. After heating for 89 hours, the reaction mixture was cooled to room temperature and partitioned between EtOAc and water. The organic phase was washed thoroughly with water (3×) followed by brine and dried over MgSO4. The solution was concentrated under vacuum and the residue chromatographed on silica gel (elution with 15:85 to 75:25 EtOAc/hexanes) to yield 2-benzyl-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one as a solid.

Workup

temperatureAfter heating for 89 hours
temperaturethe reaction mixture was cooled to room temperature
custompartitioned between EtOAc and water
washThe organic phase was washed thoroughly with water (3×)
dry with materialdried over MgSO4
concentrationThe solution was concentrated under vacuum
customthe residue chromatographed on silica gel (elution with 15:85 to 75:25 EtOAc/hexanes)

Sources & evidence

ORD record: ord-24ff5347bcb4493386095284c40c07f2
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923568B2

Reaction notes

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