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Ethanol → N-[6-(8-Cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-5-(4-fluorophenyl)nicotinamide

HRID 1748659
Notes
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Reaction equation

HRID 1748659 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:28]=1)[C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2([C:26]#[N:27])[CH2:25][CH2:24][C:19]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:18][CH2:17]2)=[CH:14][CH:15]=1)=[O:8].[F:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:26]([C:16]1([C:13]2[N:12]=[CH:11][C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:28]=[C:2]([C:33]4[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=4)[CH:3]=[N:4][CH:5]=3)=[CH:15][CH:14]=2)[CH2:25][CH2:24][C:19]2([O:23][CH2:22][CH2:21][O:20]2)[CH2:18][CH2:17]1)#[N:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 86692599HCID 86692599, compound

Product 1

HCID 86692600N-[6-(8-Cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-5-(4-fluorophenyl)nicotinamideYield 15%

Reagents, catalysts & solvents 3

HCID 178419050
HCID 178419050, compound
Catalyst
HCID 962WaterSolvent2×
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-bromo-N-[6-(8-cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]nicotinamide (213 mg), 4-fluorophenylboronic acid (63 mg), bis(triphenylphosphine)palladium (II) dichloride (100 mg) and sodium carbonate (636 mg) in a mixture of toluene (5 ml), ethanol (1 ml) and water (1 ml) was stirred at 100° C. for six hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with column chromatography to give the titled compound (31 mg).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified with column chromatography

Sources & evidence

ORD record
ord-a4c98d12a87c43ab8fc20a8df0efb0bc
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150555B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes