2-[3-(2-Methoxyethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-{5-[3-(2-Methoxy-ethoxy)-phenyl]-pyridin-2-yloxy}-azetidine-1-carboxylic acid pyrazin-2-ylamide

HRID 2097579Notes

Reaction equation

HRID 2097579 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]([N:10]1[CH2:13][CH:12]([O:14][C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][N:16]=2)[CH2:11]1)=[O:9].[CH3:22][O:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=[CH:31][CH:32]=1>>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]([N:10]1[CH2:13][CH:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([O:26][CH2:25][CH2:24][O:23][CH3:22])[CH:28]=3)=[CH:17][N:16]=2)[CH2:11]1)=[O:9]

Participants

3

Reactant 2

HCID 595587402-[3-(2-Methoxyethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66710701HCID 66710701, compound

Product 1

HCID 442188963-{5-[3-(2-Methoxy-ethoxy)-phenyl]-pyridin-2-yloxy}-azetidine-1-carboxylic acid pyrazin-2-ylamideYield 58.3%

Procedure

This compound was prepared by the method outlined for example 5 step 6. Thus 3-(5-bromo-pyridin-2-yloxy)-azetidine-1-carboxylic acid pyrazin-2-ylamide (100 mg, 0.285 mmol) was reacted with 2-[3-(2-Methoxy-ethoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (example 5 step 5, 118 mg, 0.855 mmol) to afford title compound (70 mg, 58%) as a colourless powder.

Workup

  1. customThis compound was prepared by the method

Sources & evidence

ORD record
ord-813a6c08d17c4e02bdba2cb92fa01e73
Source dataset
uspto-grants-2013_05
Patent number
US08450346B2

Reaction notes

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