3-Cyanophenylboronic acid → HCID 178419069, compound

HRID 9336

Reaction equation

HRID 9336 reaction equation
C([O:8][N:9]=[C:10]1[C:18]2([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=2)[NH:11]1)C1C=CC=CC=1.[C:25]([C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1)#[N:26]>C(#N)C1C=CC=CC=1>[C:25]([C:27]1[CH:28]=[C:29]([C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[N:9][OH:8])[C:18]23[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:30]=[CH:31][CH:32]=1)#[N:26]

Participants

4

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 178419047HCID 178419047, compound

Product 1

HCID 178419069HCID 178419069, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

3-[Spiro[cyclohexane-1,3′-[3H]indol]-(1′H)-one-2′-(O-benzyloxime)]benzonitrile[3H]indol]-5-yl]benzonitrile. Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol) and 3-cyanophenyl boronic acid (0.76 g, 5.2 mmol) according to Example 45 procedure A. The product was purified by flash silica gel chromatography (eluant: 10:0.5 hexane:ethyl acetate) to give the desired product (0.75 g, 1.8 mmol, 71%) as a viscous oil. 1H NMR (500 MHz, DMSO-d6) δ 1.41–1.81 (8H, m), 1.96–2.03 (2H, q), 5.01 (2H, s), 6.86 (1H, d), 7.28–7.33 (9H, m), 7.95–7.97 (1H, d), 8.12 (1H, s), 9.65 (1H, s); MS (ESI(−ve)) m/z 406 (M−H)−.

Workup

  1. customThe product was purified by flash silica gel chromatography (eluant: 10:0.5 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-0c8aec81ccc749b5850d7d06995e26e2
Source dataset
uspto-grants-2006_08
Patent number
US07091234B2

Linked notes

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