Sodium Carbonate → (E)-3-{3-[6-(4-Methyl-[1,4]diazepan-1-yl)pyrazin-2-yl]-phenyl}-acrylic acid methyl ester

HRID 1879665Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][CH:11]=1.Cl[C:17]1[N:22]=[C:21]([N:23]2[CH2:29][CH2:28][CH2:27][N:26]([CH3:30])[CH2:25][CH2:24]2)[CH:20]=[N:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:15])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:17]2[CH:18]=[N:19][CH:20]=[C:21]([N:23]3[CH2:29][CH2:28][CH2:27][N:26]([CH3:30])[CH2:25][CH2:24]3)[N:22]=2)[CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

[3-(E-3-methoxy-3-oxo-1-propen-1-yl)phenyl]boronic acid (125 mg, 0.61 mmol) and bistriphenylphosphinepalladium(II)chloride (30 mg, 0.057 mmol) were combined in a microwave reaction tube. Subsequently 1-(6-chloro-pyrazin-2-yl)-4-methyl-[1,4]diazepane (130 mg, 0.57 mmol) was added as a solution in DMF (8 mL) followed by an aqueous solution of Na2CO3 (2M, 3 mL, 6 mmol). The tube was sealed and the reaction mixture was heated in the microwave at 120° C. for 20 min. The reaction mixture was then filtered through a plug of celite, and purified by flash chromatography to provide the title compound (124 mg 61%); MS analysis electrospray, 353 (M+H).

Workup

customThe tube was sealed
filtrationThe reaction mixture was then filtered through a plug of celite
custompurified by flash chromatography

Sources & evidence

ORD record: ord-1576edcf610c48b5b363f6244c212689
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318723B2

Reaction notes

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