1-Butanol → HCID 86696411, compound

HRID 870709Notes

Reaction equation

[CH2:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11](Br)=[CH:12][N:13]=2)[N:10]=1)[CH:2]=[CH2:3].[CH2:15]([NH:18][C:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20])[CH:16]=[CH2:17].C(O)CCC.C(=O)([O-])[O-].[Na+].[Na+]>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:15]([NH:18][C:19](=[O:20])[C:21]1[CH:26]=[CH:25][C:24]([C:11]2[N:9]3[N:10]=[C:5]([NH:4][CH2:1][CH:2]=[CH2:3])[CH:6]=[CH:7][C:8]3=[N:13][CH:12]=2)=[CH:23][CH:22]=1)[CH:16]=[CH2:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of N-allyl-3-bromoimidazo[1,2-b]pyridazin-6-amine (365 mg, 1.44 mmol), (4-(allylcarbamoyl)phenyl)boronic acid (615 mg, 3.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (62 mg, 0.085 mmol) was added n-butanol (3 mL) and 2 M aqueous sodium carbonate (2 mL). The resulting mixture was heated at 100° C. for 5 h. The reaction was then diluted with water, extracted with ethyl acetate, and purified by silica gel column (10% methanol in ethyl acetate) followed by preparative HPLC (acetonitrile/aqueous ammonium formate, Sunfire column) to afford N-allyl-4-(6-(allylamino)imidazo[1,2-b]pyridazin-3-yl)benzamide as a white solid: 1H NMR (METHANOL-d4) δ: 8.30-8.33 (d, J=8.4 Hz, 2H), 7.94 (d, J=8.4 Hz, 2H), 7.67 (d, J=9.6 Hz, 1H), 6.78 (d, J=9.6 Hz, 1H), 5.9-6.2 (m, 2H), 5.1-5.4 (m, 4H), 4.00 (m, 4H); LRMS (ESI) m/z 334.2 [(M+H)+, calcd for C19H19N5O 333.4]

Workup

extractionextracted with ethyl acetate
custompurified by silica gel column (10% methanol in ethyl acetate)

Sources & evidence

ORD record: ord-61a4367c37664f40af47e51423b1a838
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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