Potassium Carbonate → HCID 86696467, compound

HRID 870758Notes

Reaction equation

[C:1]([O:5][C:6](=[O:24])[N:7]([CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20](Br)=[CH:21][N:22]=3)[N:19]=2)[CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[N:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:24])[N:7]([CH3:8])[CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([C:28]4[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=4)=[CH:21][N:22]=3)[N:19]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of [1-(3-bromo-imidazo[1,2-b]pyridazin-6-yl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (100 mg, 0.25 mmol), 4-pyridinylboronic acid (40 mg, 0.33 mmol), K2CO3 (104 mg, 0.75 mmol) and dichlorobis(triphenylphosphine)palladium(II) (8.8 mg, 0.013 mmol) in MeCN/water (3.2 ml/0.8 ml) was heated in a microwave at 150° C. for 15 min. The water layer was removed and the organic layer was diluted with MeCN and filtered. The filtrate was subjected to preparative HPLC to give the titled compound (25.3 mg). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.50-1.55 (m, 9H) 2.22-2.32 (m, 2H) 2.89 (s, 3H) 3.46-3.57 (m, 2H) 3.72-3.80 (m, 2H) 4.91 (t, J=7.61 Hz, 1H) 6.95 (d, J=9.92 Hz, 1H) 7.77 (d, J=9.70 Hz, 1H) 8.11 (s, 1H) 8.23-8.27 (m, 2H) 8.53-8.58 (m, 2H). LRMS (ESI) m/z 395.2 [(M+H)]+, calc'd for C21H26N6O2: 394.48.

Workup

customThe water layer was removed
additionthe organic layer was diluted with MeCN
filtrationfiltered

Sources & evidence

ORD record: ord-f27a6c042d8743f8b5a4309e7db4119b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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