1-Fluoro-3-iodo-5-nitrobenzene → 6-(3-Fluoro-5-nitrophenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 2121770Notes

Reaction equation

HRID 2121770 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.[F:24][C:25]1[CH:26]=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=[C:29](I)[CH:30]=1>>[F:24][C:25]1[CH:26]=[C:27]([N+:32]([O-:34])=[O:33])[CH:28]=[C:29]([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:30]=1

Participants

3

Reactant 2

HCID 2590861-Fluoro-3-iodo-5-nitrobenzeneHCID 10615401(1-(tert-Butoxycarbonyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)boronic acid

Product 1

HCID 108050526-(3-Fluoro-5-nitrophenyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 69.1%

Procedure

This compound was prepared according to General Method 2 (EXAMPLE 9 ) from Compound 9 (140.2 mg, 0.44 mmol) and 5-fluoro-3-nitroiodobenzene (117.6 mg, 0.44 mmol). The crude material was purified by flash column chromatography (150 ml silica, hexane to 20% acetone/hexane) followed by a second flash column chromatography (100 mL silica, hexane to 20% acetone/hexane) to afford 95 mg (69%) of Compound 280. Data for Compound 280: 1H NMR (400 MHz, acetone-d6) 8.22 (app t, J=3.0, 1.5, 1H), 7.78 (m, 1H), 7.43 (d, J=2.2, 1H), 7.38 (dd, J=8.4, 2.3, 1H), 6.61 (d, J=8.3, 1H), 5.58 (s, 1H), 5.40 (s, 1H), 2.05 (s, 3H), 1.29 (s, 6H).

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by flash column chromatography (150 ml silica, hexane to 20% acetone/hexane)

Sources & evidence

ORD record
ord-263be9228e0e41d5a184eb4687e3d06d
Source dataset
uspto-grants-2004_02
Patent number
US06696459B1

Reaction notes

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