Potassium Carbonate → HCID 86696394, compound

HRID 870691Notes

Reaction equation

Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[CH:30]=[N:29][CH:28]=[CH:27]3)O1.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>[CH2:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH:30]=[N:29][CH:28]=[CH:27]4)=[CH:3][N:4]=2)[N:7]=1)[CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (3-bromo-imidazo[1,2-b]pyridazin-6-yl)-butyl-amine (100 mg, 0.37 mmol), 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline (from part A, ˜1 mmol), K2CO3 (153 mg, 1.11 mmol) and dichlorobis(triphenylphosphine)palladium(II) (13 mg, 0.019 mmol) in MeCN/water (4 ml/1 ml) was heated in a microwave at 150° C. for 15 min. The water layer was removed and the reaction mixture was diluted with MeCN (3 ml) and filtered. The filtrate was subjected to preparative HPLC to give the titled compound (80.8 mg). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.03 (t, J=7.33 Hz, 3H) 1.53 (dq, J=14.97, 7.39 Hz, 2H) 1.74-1.81 (m, 2H) 3.48-3.54 (m, 2H) 4.58 (t, J=5.05 Hz, 1H) 6.54 (d, J=9.60 Hz, 1H) 7.68 (d, J=5.56 Hz, 1H) 7.75 (d, J=9.60 Hz, 1H) 8.01-8.05 (m, 2H) 8.25 (dd, J=8.72, 1.64 Hz, 1H) 8.55 (d, J=5.81 Hz, 1H) 8.86 (s, 1H) 9.25 (s, 1H). LRMS (ESI) m/z 318.2 [(M+H)]+, calc'd for C19H19N5: 317.40.

Workup

customThe water layer was removed
additionthe reaction mixture was diluted with MeCN (3 ml)
filtrationfiltered

Sources & evidence

ORD record: ord-0ffca20628a94011b35057cf30cb9520
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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