Water → 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-1-methyl-cyclohexanol

HRID 1257759Notes

Reaction equation

[C:1]1([S:7]([N:10]2[CH:21]=[CH:20][C:19]3[C:11]2=[N:12][CH:13]=[C:14]2[C:18]=3[N:17]([CH:22]3[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]3)[N:16]=[N:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br].[CH3:30][Mg].O>O1CCCC1>[C:1]1([S:7]([N:10]2[CH:21]=[CH:20][C:19]3[C:11]2=[N:12][CH:13]=[C:14]2[C:18]=3[N:17]([CH:22]3[CH2:23][CH2:24][C:25]([CH3:30])([OH:28])[CH2:26][CH2:27]3)[N:16]=[N:15]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanone (400 mg, 1.01 mmol) in anhydrous tetrahydrofuran (20 mL) was added dropwise methylmagnesium bromine (3 M in diethyl ether, 2.3 mL, 7.07 mmol), followed by stirring at 0° C. for 30 minutes under nitrogen. The reaction was warmed to room temperature and stirred for another 90 minutes. The resulting mixture was poured into water and extracted with ethyl acetate. The organic solution was used for the next step. LCMS (Method K, ESI): RT=1.318 min and 1.359, m+H=411.8.

Workup

temperatureThe reaction was warmed to room temperature
stirringstirred for another 90 minutes
extractionextracted with ethyl acetate

Sources & evidence

ORD record: ord-3cc46c5071d847278e2a9172d0e880b2
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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