(1-(tert-Butoxycarbonyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)boronic acid → 6-(3-Cyano-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline

HRID 1604789Notes

Reaction equation

HRID 1604789 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14](B(O)O)=[CH:15][CH:16]=2)[C:11]([CH3:21])=[CH:10][C:9]1([CH3:23])[CH3:22])=O)(C)(C)C.Br[C:25]1[C:26]([CH3:33])=[C:27]([CH:30]=[CH:31][CH:32]=1)[C:28]#[N:29]>>[C:28]([C:27]1[C:26]([CH3:33])=[C:25]([C:14]2[CH:13]=[C:12]3[C:17](=[CH:16][CH:15]=2)[NH:8][C:9]([CH3:22])([CH3:23])[CH:10]=[C:11]3[CH3:21])[CH:32]=[CH:31][CH:30]=1)#[N:29]

Participants

3

Reactant 2

HCID 10615401(1-(tert-Butoxycarbonyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)boronic acidHCID 234335373-Bromo-2-methylbenzonitrile

Product 1

HCID 234334976-(3-Cyano-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinolineYield 20.2%

Procedure

This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (56.5 mg, 0.18 mmol) and 3-bromo-2-methylbenzonitrile (34.8 mg, 0.18 mmol). The crude material was purified by flash column chromatography (50 ml silica, hexane to 20% acetone/hexane) followed by a second flash column chromatography (75 mL silica, hexane to 20% acetone/hexane) to afford 10.5 mg (20%) of Compound 278. Data for Compound 278: 1H NMR (400 MHz, acetone-d6) 7.59 (dd, J=7.7, 0.9, 1 H), 7.48 (dd, J=7.8, 0.8, 1 H), 7.36 (t, J=15.3, 7.7, 1 H), 6.99 (d, J=1.8 1 H), 6.91 (dd, J=8.1, 1.9, 1 H), 6.58 (d, J=8.1, 1 H), 5.37 (s, 1 H), 5.30 (s, 1 H), 2.48 (s, 3 H), 1.97 (s, 3 H), 1.30 (s, 6 H).

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by flash column chromatography (50 ml silica, hexane to 20% acetone/hexane)

Sources & evidence

ORD record
ord-c5af144c58ce40eaa0cb011eb67e8ac0
Source dataset
uspto-grants-1999_11
Patent number
US05994544

Reaction notes

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