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Sodium Bicarbonate → N-(2-t-Butoxycarbonylaminophenyl)-4-(3-cyano-5-formylpyridin-2-yl)benzamide

HRID 599520
Notes
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Reaction equation

HRID 599520 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:34]1[C:39]([C:40]#[N:41])=[CH:38][C:37]([CH:42]=[O:43])=[CH:36][N:35]=1.C(=O)([O-])O.[Na+]>COCCOC>[CH3:20][CH2:19][CH2:18][CH:17]([CH3:22])[CH3:16].[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:18]=[CH:19][C:20]([C:34]2[C:39]([C:40]#[N:41])=[CH:38][C:37]([CH:42]=[O:43])=[CH:36][N:35]=2)=[CH:21][CH:22]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 197106832-Chloro-5-formylnicotinonitrileHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 2

HCID 78922-MethylpentaneHCID 86624985N-(2-t-Butoxycarbonylaminophenyl)-4-(3-cyano-5-formylpyridin-2-yl)benzamideYield 101.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5,tetramethyl-1,3,2,-dioxaborolan-2-yl)benzamide (1.2 g, 2.74 mmol; prepared as described in international patent publication number wo03/087057, method 13, page 60), 2-chloro-3-cyano-5-formylpyridine [prepared as described in de 4429465 a1 (1996)] (456 mg, 2.74 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex 112 mg, 0.137 mmol), 1,2-dimethoxyethane (12 ml) and a saturated aqueous solution of sodium hydrogen carbonate (6 ml) were stirred at 60° c. under an atmosphere of nitrogen for 7.5 hours. the mixture was allowed to cool before being partitioned between dichloromethane and water. the organics were separated, dried over sodium sulfate, filtered and evaporated. the crude product was purified by chromatography on silica eluting with 30:70 to 40:60 ethyl acetate: isohexane to afford the title compound as a cream solid (615 mg, 51%); nmr spectrum: (dmso-d6) 1.45 (s, 9h), 7.18 (m, 2h), 7.56 (m, 2h), 8.10 (d, 2h), 8.17 (d, 2h), 8.70 (s, 1h), 8.90 (d, 1h), 9.39 (d, 1h), 9.97 (s, 1h), 10.18 (s, 1h); mass spectrum: m+na+ 465.

Workup

  1. temperatureto cool
  2. custombefore being partitioned between dichloromethane and water
  3. customthe organics were separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude product was purified by chromatography on silica eluting with 30:70 to 40:60 ethyl acetate

Sources & evidence

ORD record
ord-e204b7b7e0244b8db9bfa581380619a5
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07897778B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes