1-(Trifluoromethylsulfonyloxy)-2,6-dimethyl-1-cyclohexene → (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(2,6-dimethyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone

HRID 1794008Notes

Reaction equation

HRID 1794008 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20](B4OC(C)(C)C(C)(C)O4)=[C:19]([CH3:32])[CH:18]=3)=[O:16])[CH2:6][C:5]=12.FC(F)(F)S(O[C:39]1[CH:44]([CH3:45])[CH2:43][CH2:42][CH2:41][C:40]=1[CH3:46])(=O)=O>>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:39]4[CH:44]([CH3:45])[CH2:43][CH2:42][CH2:41][C:40]=4[CH3:46])=[C:19]([CH3:32])[CH:18]=3)=[O:16])[CH2:6][C:5]=12

Participants

3

Reactant 2

HCID 125721641-(Trifluoromethylsulfonyloxy)-2,6-dimethyl-1-cyclohexeneHCID 22219714(10,11-Dihydro-5H-pyrrolo [2,1-c][1,4] benzodiazepin-10-yl)-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

Product 1

HCID 10223296(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(2,6-dimethyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone

Procedure

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone of Example 2, Step B (0.500 g, 1.17 mmol) and 2,6-dimethyl-cyclohex-1-en-1-yl trifluoromethanesulfonate (0.401 g, 1.29 mmol) were reacted in the manner of Example 2, Step C. Purification by flash column chromatography on silica gel, eluting with 30% ethyl acetate in hexane, followed by recrystallization from petroleum ether (−20° C.) afforded the title compound as white crystals, m.p. 133–135° C.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with 30% ethyl acetate in hexane
  3. customfollowed by recrystallization from petroleum ether (−20° C.)

Sources & evidence

ORD record
ord-8e15a8092c80472083b0f8631ecf150c
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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