Methyl 4-[bromo(3-cyanophenyl)methyl]benzoate → Methyl 4-((S)-(3-cyanophenyl){3-[(1S)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl}methyl)benzoate

HRID 602995Notes

Reaction equation

HRID 602995 reaction equation
Br[CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[F:21][C:22]1[CH:23]=[C:24]([C@H:29]([CH:34]2[CH2:37][NH:36][CH2:35]2)[C:30]([F:33])([CH3:32])[CH3:31])[CH:25]=[C:26]([F:28])[CH:27]=1>>[C:19]([C:15]1[CH:14]=[C:13]([C@@H:2]([N:36]2[CH2:37][CH:34]([C@@H:29]([C:24]3[CH:23]=[C:22]([F:21])[CH:27]=[C:26]([F:28])[CH:25]=3)[C:30]([F:33])([CH3:31])[CH3:32])[CH2:35]2)[C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=2)[CH:18]=[CH:17][CH:16]=1)#[N:20]

Participants

3

Reactant 2

HCID 67055333Methyl 4-[bromo(3-cyanophenyl)methyl]benzoateHCID 670553593-[(1S)-1-(3,5-Difluorophenyl)-2-fluoro-2-methylpropyl]azetidine

Product 1

HCID 67055327Methyl 4-((S)-(3-cyanophenyl){3-[(1S)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl}methyl)benzoate

Procedure

The title compound was prepared methyl 4-[bromo(3-cyanophenyl)methyl]benzoate and 3-[(1S)-1-(3,5-difluorophenyl)-2-fluoro-2-methylpropyl]azetidine (Step 1, Preparation 15) by the procedure described in Step 2 of Preparation 15. The product was purified by chromatography on an AD column using 30% isopropanol-heptane to afford the title compound; 1H-NMR(CDCl3) δ 1.25 (t, J=22 Hz, 6H), 2.33 (t, J=6.5 Hz, 1H), 2.83-2.89 (m, 2H), 3.05-3.22 (m, 2H), 3.65 (m, 1H), 3.92 (s, 3H), 4.34 (s, 1H), 6.68-6.71 (m, 3H), 7.21-7.8 (m, 8H); Mass Spectrum: m/e=493 (M+1).

Workup

  1. customdescribed in Step 2 of Preparation 15
  2. customThe product was purified by chromatography on an AD column

Sources & evidence

ORD record
ord-fd89f94f09b14d0eb53746f6c7c3e41e
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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