3-Chloro-5-cyanophenylboronic acid, pinacol ester → US9000184, 10, isomer 1

HRID 1468242Notes

Reaction equation

HRID 1468242 reaction equation
Br[C:2]1[CH:24]=[C:23]2[C:5]([CH2:6][CH2:7][C:8]3([C:16]42[N:20]=[C:19]([NH2:21])[C:18]([CH3:22])=[N:17]4)[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][CH2:9]3)=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:33]=1)[C:29]#[N:30]>>[NH2:21][C:19]1[C:18]([CH3:22])=[N:17][C:16]2([C:23]3[C:5](=[CH:4][CH:3]=[C:2]([C:32]4[CH:31]=[C:28]([CH:27]=[C:26]([Cl:25])[CH:33]=4)[C:29]#[N:30])[CH:24]=3)[CH2:6][CH2:7][C:8]32[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][CH2:9]3)[N:20]=1

Participants

3

Reactant 2

HCID 532171293-Chloro-5-cyanophenylboronic acid, pinacol ester2×HCID 72714746US9000184, 5, isomer 1

Product 1

HCID 72714844US9000184, 10, isomer 1

Procedure

The title compound was prepared following the procedure described for Example 2, starting from 7′-bromo-4-methoxy-5″-methyl-3′,4′-dihydrodispiro[cyclohexane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 5, 125 mg, 0.32 mmol) and 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (Intermediate 4, 93 mg, 0.35 mmol). The product was purified using preparative chromatography followed by concentration of the fractions, extraction of the remaining aqueous phase with DCM, washing the organic layer with water and concentration and drying in vacuo at 50° C. for 2 days to give:

Workup

  1. customThe product was purified
  2. extractionfollowed by concentration of the fractions, extraction of the remaining aqueous phase with DCM
  3. washwashing the organic layer
  4. concentrationwith water and concentration
  5. customdrying in vacuo at 50° C. for 2 days
  6. customto give

Sources & evidence

ORD record
ord-c35a426b2f1d4d68828dbaaa5106e234
Source dataset
uspto-grants-2015_04
Patent number
US09000184B2

Reaction notes

Loading…