2-(3,5-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 7'-(3,5-Difluorophenyl)-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

HRID 1468236Notes

Reaction equation

HRID 1468236 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([F:8])[CH:7]=1.Br[C:19]1[CH:36]=[C:35]2[C:22]([CH2:23][CH2:24][C:25]3([C:28]42[N:32]=[C:31]([NH2:33])[C:30]([CH3:34])=[N:29]4)[CH2:27][CH2:26]3)=[CH:21][CH:20]=1>>[F:8][C:6]1[CH:5]=[C:4]([C:19]2[CH:36]=[C:35]3[C:22]([CH2:23][CH2:24][C:25]4([C:28]53[N:32]=[C:31]([NH2:33])[C:30]([CH3:34])=[N:29]5)[CH2:26][CH2:27]4)=[CH:21][CH:20]=2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 467393012-(3,5-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 727146587'-Bromo-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

Product 1

HCID 727147447'-(3,5-Difluorophenyl)-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amineYield 61.5%

Procedure

The title compound was prepared following the procedure described for Example 2, starting from (3,5-difluorophenyl)boronic acid pinacol ester (113 mg, 0.47 mmol) and 7′-bromo-5″-methyl-3′,4′-dihydrodispiro[cyclopropane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 1, 100 mg, 0.31 mmol). Purification by flash silica gel chromatography using a step wise gradient of CHCl3/MeOH (40:1-30:1-20:1) and preparative HPLC gave the title compound (67 mg, 61% yield).

Workup

  1. customThe title compound was prepared
  2. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-0ca4856d06b548c482544606be12f78c
Source dataset
uspto-grants-2015_04
Patent number
US09000184B2

Reaction notes

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