Ethanol → (4-(Pyridazin-4-yl)phenyl)methanamine

HRID 711215Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][N:16]=[N:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N:15]1[CH:14]=[CH:13][C:18]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][NH2:1])=[CH:4][CH:5]=2)=[CH:17][N:16]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a sealed tube was added 4-(aminomethyl)phenylboronic acid 1-1 (1.87 g, 10 mmol), 4-bromopyridazine 1-2 (1.58 g, 10 mmol), Pd(PPh3)4 (230 mg, 0.2 mmol), saturated Na2CO3 (15 mL), ethanol (15 mL) and toluene (45 mL). The reaction was heated to 110° C. and stirred for 2 hours. The reaction was cooled down to room temperature. The solvent was removed by rotary evaporation. The residue was dissolved in 10% methanol in DCM. The salt was removed by filtration. The filtrate was dried. The crude product was purified by silica-gel flash chromatography, eluted with 10% methanol in DCM to give (4-(pyridazin-4-yl)phenyl)methanamine 1-3 as off-white solid. MS m/z 186.2 (M+1).

Workup

temperatureThe reaction was cooled down to room temperature
customThe solvent was removed by rotary evaporation
dissolutionThe residue was dissolved in 10% methanol in DCM
customThe salt was removed by filtration
customThe filtrate was dried
customThe crude product was purified by silica-gel flash chromatography
washeluted with 10% methanol in DCM

Sources & evidence

ORD record: ord-e5ca96c5f27c441692b3f8858e3d87f7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181235B2

Reaction notes

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