Boron tribromide → [4-(2-Azepan-1-yl-ethoxy)-phenyl]-[2-(2,4-difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-methanone

HRID 1513960Notes

Reaction equation

HRID 1513960 reaction equation
FC1C=C(F)C=CC=1C1C=CC2C(=CC=C(O)C=2)C=1C(C1C=CC(OCCN2CCCCC2)=CC=1)=O.[N:37]1([CH2:44][CH2:45][O:46][C:47]2[CH:52]=[CH:51][C:50]([C:53]([C:55]3[C:64]4[C:59](=[CH:60][C:61]([O:65]C)=[CH:62][CH:63]=4)[CH:58]=[CH:57][C:56]=3[C:67]3[CH:72]=[CH:71][C:70]([F:73])=[CH:69][C:68]=3[F:74])=[O:54])=[CH:49][CH:48]=2)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.B(Br)(Br)Br>>[N:37]1([CH2:44][CH2:45][O:46][C:47]2[CH:52]=[CH:51][C:50]([C:53]([C:55]3[C:64]4[C:59](=[CH:60][C:61]([OH:65])=[CH:62][CH:63]=4)[CH:58]=[CH:57][C:56]=3[C:67]3[CH:72]=[CH:71][C:70]([F:73])=[CH:69][C:68]=3[F:74])=[O:54])=[CH:49][CH:48]=2)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 11466453[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[2-(2,4-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-methanoneHCID 67004951[2-(2,4-Difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Product 1

HCID 67004715[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[2-(2,4-difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-methanoneYield 75%

Procedure

By the standard demethylation procedure found in the preparation of [2-(2,4-difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone, [4-(2-azepan-1-yl-ethoxy)-phenyl]-[2-(2,4-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-methanone (1.1 g, 2.1 mmol) is demethylated with BBr3 (1.0 mL, 10.5 mmol) to afford crude product. Purify on silica gel (0% to 5% methanol in methylene chloride) to yield 790 mg (75%) of the title compound: mass spectrum (ion spray) m/z=502.3 (M+H).

Workup

  1. customto afford crude product
  2. customPurify on silica gel (0% to 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-25b0df30719940b183b0d2d6c64253ce
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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