1-Naphthyl trifluoromethanesulfonate → (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(3,4-dihydro-naphthalen-1-yl)-phenyl]-methanone

HRID 1793980Notes

Reaction equation

HRID 1793980 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)=[CH:19][C:18]=3[Cl:32])=[O:16])[CH2:6][C:5]=12.FC(F)(F)S(O[C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[CH:41][CH:40]=1)(=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:42]4[C:43]5[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=5)[CH2:39][CH2:40][CH:41]=4)=[CH:19][C:18]=3[Cl:32])=[O:16])[CH2:6][C:5]=12

Participants

3

Reactant 2

HCID 3788841-Naphthyl trifluoromethanesulfonateHCID 22219716(10,11-Dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-[2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

Product 1

HCID 10297680(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(3,4-dihydro-naphthalen-1-yl)-phenyl]-methanoneYield 96.3%

Procedure

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone of Example 10, Step B (0.300 g, 0.668 mmol) and naphthalen-1-yl trifluoromethanesulfonate (0.205 g, 0.735 mmol) were reacted by the procedure described in Example 1, Step F. The crude product was purified by flash column chromatography on silica gel, eluting with 30% ethyl acetate in hexane to afford a clear oil. The oil was recrystallized from diethyl ether/petroleum ether to afford white crystals (0.290 g), m.p. 174–176° C.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with 30% ethyl acetate in hexane
  3. customto afford a clear oil
  4. customThe oil was recrystallized from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-59c8aec5d758495ab0cb222e7adbc213
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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