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Sodium Bicarbonate → N-(2-t-Butoxycarbonylaminophenyl)-4-(3-cyanopyridin-2-yl)benzamide

HRID 599518
Notes
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Reaction equation

HRID 599518 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].Br[C:34]1[N:41]=[CH:40][CH:39]=[CH:38][C:35]=1[C:36]#[N:37].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:22]=[CH:21][C:20]([C:34]2[C:35]([C:36]#[N:37])=[CH:38][CH:39]=[CH:40][N:41]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 8171532-Bromopyridine-3-carbonitrileHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 2

HCID 78922-MethylpentaneHCID 67269547N-(2-t-Butoxycarbonylaminophenyl)-4-(3-cyanopyridin-2-yl)benzamideYield 113.1%

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 (400 mg, 0.913 mmol; prepared as described in international patent publication number wo03/087057, method 13, page 60), 2-bromonicotinonitrile (167 mg, 0.913 mmol), tetrakis(triphenylphosphine)palladium[0] (50 mg, 0.043 mmol), 1,2-dimethoxyethane (4 ml) and a saturated aqueous solution of sodium hydrogen carbonate (2 ml) were stirred at 100° c. under an atmosphere of nitrogen in a microwave for 130 mins. 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 60:40 ethyl acetate: isohexane to afford the title compound as a white solid (214 mg, 57%); nmr spectrum: (dmso-d6) 1.45 (s, 9h), 7.18 (m, 2h), 7.57 (m, 1h), 7.66 (dd, 1h), 8.01 (d, 2h), 8.13 (d, 2h), 8.47 (dd, 1h), 8.73 (s, 1h), 8.98 (d, 1h), 9.97 (s, 1h); mass spectrum: m+h+415.

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 60:40 ethyl acetate

Sources & evidence

ORD record
ord-5d0f16369bc14700b1d5aae13e74265e
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