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Toluene → HCID 67366556, compound

HRID 2189207
Notes
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Reaction equation

HRID 2189207 reaction equation
C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:15]1[N:24]=[C:23]([NH:25][C@H:26]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1.[CH3:38][C:39]1[CH:40]=[CH:41][C:42]([O:48][CH3:49])=[C:43](B(O)O)[CH:44]=1>O.C(O)CCC>[CH3:49][O:48][C:42]1[CH:43]=[CH:44][C:39]([CH3:38])=[CH:40][C:41]=1[C:15]1[N:24]=[C:23]([NH:25][C@H:26]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2773485(2-Methoxy-5-methylphenyl)boronic acidHCID 58394359HCID 58394359, compound

Product 1

HCID 67366556HCID 67366556, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 263
1-Butanol
Solvent
HCID 962WaterSolvent

Procedure

A mixture of toluene (1.8 mL), n-butanol (3 mL) and 2M Na2CO3 (3 mL) was degassed with a stream of nitrogen for 20 minutes. The mixture was transferred onto a degassed mixture of (S)-tert-butyl 3-(2-chloroquinazolin-4-ylamino)pyrrolidine-1-carboxylate (0.300 g, 0.86 mmol), palladium tetrakistriphenyl phosphine (0.0718 g, 0.06 mmol) and 5-methyl-2-methoxyphenylboronic acid (0.143 g, 0.86 mmol) and the solution was heated at reflux. After 17 hours the reaction was cooled, diluted with water (20 mL), and extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine (20 mL), dried (MgSO4), and concentrated. Silica chromatography (6:1-1:1 petroleum ether/ethyl acetate) gave the title compound as a colourless solid (0.329 g, 99%).

Workup

  1. customwas degassed with a stream of nitrogen for 20 minutes
  2. temperaturethe solution was heated
  3. temperatureat reflux
  4. temperatureAfter 17 hours the reaction was cooled
  5. extractionextracted with ethyl acetate (2×20 mL)
  6. washThe combined organic extracts were washed with brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2e2dee760f9249cba88513f4b177835b
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324226B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes