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Diisopropylethylamine → Tert-butyl (+/-)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoate

HRID 2281157
Notes
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Reaction equation

HRID 2281157 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][C:4]([C:6]1[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:8][CH:7]=1)=O.[CH3:20][C:21]1[CH:22]=[N+:23]([O-])[C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2.C([N:35](C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>ClCCl.C(=O)(O)[O-].[Na+]>[CH3:1][CH:2]([CH3:19])[CH2:3][CH:4]([C:6]1[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:8][CH:7]=1)[NH:35][C:22]1[C:21]([CH3:20])=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 70214663-Methylquinoline N-oxideHCID 71239698Tert-butyl 4-(3-methylbutanoyl)benzoate

Product 1

HCID 71243814Tert-butyl (+/-)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoate

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl (+/−)-4-(3-methylbutanoyl)benzoate (527 mg, 2.00 mmol) and 3-methylquinoline N-oxide (318 mg, 2.00 mmol) in dichloromethane (8.0 mL) was added diisopropylethylamine (1.31 mL, 7.50 mmol) followed by bromotripyrrolidinophosphonium hexafluorophosphate (1.18 g, 2.50 mmol). The solution was stirred at room temperature for 18 hours then diluted with sat. aq sodium bicarbonate (20 mL). The mixture was extracted with ethyl acetate (3×20 mL). The combined organics were dried over anhydrous Na2SO4 and filtered, and the filtrate was concentrated. Purification by silica gel flash chromatography (ethyl acetate/heptane) gave tert-butyl (+/−)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoate as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.94 (d, J=8.2 Hz, 2 H), 7.63 (d, J=8.2 Hz, 1 H), 7.59 (s, 1 H), 7.54-7.48 (m, 3 H), 7.47-7.41 (m, 1 H), 7.19-7.13 (m, 1 H), 5.56 (q, J=7.4 Hz, 1 H), 4.73 (d, J=7.0 Hz, 1 H), 2.28 (s, 3 H), 1.94-1.83 (m, 1 H), 1.81-1.70 (m, 1 H), 1.70-1.60 (m, 1 H), 1.57 (s, 9 H), 1.04 (d, J=6.6 Hz, 3 H), 0.97 (d, J=6.6 Hz, 3 H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organics were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customPurification by silica gel flash chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-ef581192a10e41cdaac9472e07d6e500
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139538B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes