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

HRID 1948557Notes

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]

Participants

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

temperatureThe mixture was cooled to RT
washThe mixture was washed with sat. aq. NH4Cl
dry with materialdried over Na2SO4
filtrationfiltered
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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