3-Bromo-5-fluorobenzonitrile → 6-(3-Cyano-5-fluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline

HRID 2121767Notes

Reaction equation

HRID 2121767 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[CH:26]=[C:27]([CH:30]=[C:31]([F:33])[CH:32]=1)[C:28]#[N:29]>>[C:28]([C:27]1[CH:26]=[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]=[C:31]([F:33])[CH:30]=1)#[N:29]

Participants

3

Reactant 2

HCID 27833303-Bromo-5-fluorobenzonitrileHCID 10615401(1-(tert-Butoxycarbonyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)boronic acid

Product 1

HCID 98390136-(3-Cyano-5-fluorophenyl)-1,2-dihydro-2,2,4-trimethylquinolineYield 38.6%

Procedure

This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (46.3 mg, 0.14 mmol) and 3-bromo-5-fluorobenzonitrile (29.1 mg, 0.14 mmol). The crude material was purified by recrystallization from hexane to afford 15.8 mg (37%) of Compound 271. Data for Compound 271: 1H NMR (400 MHz, acetone-d6) 7.83 (app t, J=1.3, 1H), 7.68 (dd, J=10.6, 4.0, 1H), 7.43 (d, J=2.0, 1H), 7.41 (dd, J=2.2, 1.2 1H) 7.35 (dd, J=8.3, 2.2, 1H), 6.59 (d, J=8.4, 1H), 5.35 (br s, 1H), 5.39 (s, 1H), 2.04 (s, 3H), 1.28 (s, 6H).

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by recrystallization from hexane

Sources & evidence

ORD record
ord-c922ba939c1d47f88c32484a19d7ff90
Source dataset
uspto-grants-2004_02
Patent number
US06696459B1

Reaction notes

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