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Ethyl Acetate → 4'-Fluorobiphenyl-2-carboxylic acid (2-acetylamino-indan-5-yl)-amide

HRID 1531274
Notes
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Reaction equation

HRID 1531274 reaction equation
[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3Br)[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2].[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(OCC)(=O)C>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:14][C:15]([C:16]3[C:17]([C:28]4[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=4)=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:23])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 21253364N-(2-acetylamino-indan-5-yl)-2-bromo-benzamide

Product 1

HCID 543765954'-Fluorobiphenyl-2-carboxylic acid (2-acetylamino-indan-5-yl)-amide

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of N-(2-acetylamino-indan-5-yl)-2-bromo-benzamide (the title C compound; 0.150 g, 0.40 mmol) and 4-fluorobenzeneboronic acid (0.0.84 g, 0.60 mmol) in DME (7 mL) is added PdCl2(dppf) (0.010 g, 0.012 mmol) followed by K3PO4 (0.25 g, 1.20 mmol). The reaction mixture is degassed and heated at reflux under N2 atmosphere for 16 h. After cooling to room temperature, the reaction mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give a tan solid. Trituration with ethyl acetate gives 4′-fluorobiphenyl-2-carboxylic acid (2-acetylamino-indan-5-yl)-amide as a grey solid, mp 218-220° C. MS (ES+), m/z 389 (M+1).

Workup

  1. customThe reaction mixture is degassed
  2. temperatureheated
  3. temperatureat reflux under N2 atmosphere for 16 h
  4. additionthe reaction mixture is diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customto give a tan solid

Sources & evidence

ORD record
ord-321e127da22f4698a5198e740bd6dc1a
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06197798B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes