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Water → 5-Bromo-N-(3,4-dimethoxybenzyl)-2-pyridin-3-ylbenzamide

HRID 1948557
Notes
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Reaction equation

HRID 1948557 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:8].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C1COCC1.CCOC(C)=O.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(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 45725783HCID 45725783, compound

Product 1

HCID 584084115-Bromo-N-(3,4-dimethoxybenzyl)-2-pyridin-3-ylbenzamide

Reagents, catalysts & solvents 3

HCID 178418807
HCID 178418807, compound
Catalyst
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 1-2 (100 mg, 0.210 mmol, 1.0 equiv) in THF (2 ml) in a microwave vial was treated with pyridine-3-boronic acid pinacol ester (47.4 mg, 0.231 mmol, 1.1 equiv), cesium carbonate (163 mg, 0.500 mmol, 2.4 equiv), PdCl2(dppf)-CH2Cl2 adduct (17.15 mg, 0.021 mmol, 0.1 equiv), and 0.5 mL water. The mixture was heated to 120° C. in a microwave reactor for 10 min. The mixture was cooled to RT and diluted with EtOAc. The mixture was washed with sat. aq. NH4Cl, dried over Na2SO4, filtered and concentrated. The crude material (1-3) was used as is in the next step. ESI+ MS [M+H]+ C21H19BrN2O3: 428.0 found, 427.3 required.

Workup

  1. temperatureThe mixture was cooled to RT
  2. washThe mixture was washed with sat. aq. NH4Cl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-882cae3045aa497caca54eac90add8d7
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399494B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes