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Diazomethane → 6-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)cyclopropyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one

HRID 77488
Notes
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Reaction equation

HRID 77488 reaction equation
[F:1][CH:2]([F:38])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[N:25]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:24](=[O:37])[CH:23]=[CH:22]4)=[CH:13][N:12]=2)=[CH:6][CH:5]=1.[N+](=[CH2:41])=[N-]>C(OCC)C>[F:38][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH:17]3[CH2:41][CH:18]3[C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[N:25]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:24](=[O:37])[CH:23]=[CH:22]4)=[CH:13][N:12]=2)=[CH:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 86679781(E)-6-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one

Product 1

HCID 866797806-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)cyclopropyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-oneYield 49%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent
2×

Conditions

Temperature
-10 °C

Procedure

To a stirred solution of (E)-6-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one (0.15 g, 0.280 mmol) in diethyl ether (10 mL) was added PdOAc2 (6.28 mg, 0.028 mmol). The reaction mixture was cooled to −10° C., and a cold solution of diazomethane in ether (generated from aqueous KOH (0.45 g) and NMU (0.6 g) at −15° C.) was added. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was filtered through celite, diluted with diethyl ether, and washed with water and saturated NaCl solution. The organic layer was dried over sodium sulfate, concentrated, and purified by flash chromatography on silica gel column using 15% ethyl acetate in hexane to give 6-(2-(2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)cyclopropyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one as a yellow gum (0.075 g, 49%). LCMS: RT 2.317 min, (M+H) 551.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. additiondiluted with diethyl ether
  3. washwashed with water and saturated NaCl solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel column

Sources & evidence

ORD record
ord-04418496064546c3b4e228744ccee340
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841301B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes