Potassium Carbonate → HCID 71525519, compound

HRID 1755297Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2([CH3:17])[CH3:16])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:16][C:12]1([CH3:17])[CH2:13][CH2:14][CH2:15][N:11]1[C:4]1[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=[C:2]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-chloro-8-(2,2-dimethylpyrrolidin-1-yl)imidazo[1,2-b]pyridazine (140 mg, 0.56 mmol), phenylboronic acid (103 mg, 0.84 mmol), Pd2(dba)3 (34 mg, 0.06 mmol), X-phos (114 mg, 0.24 mmol) and K2CO3 (235 mg, 1.70 mmol) in dioxane (10 mL) and water (1 mL) was heated to 100° C. with stirring for 4 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=200:1) to give 8-(2,2-dimethylpyrrolidin-1-yl)-6-phenylimidazo[1,2-b]pyridazine (65 mg, 40%) as a light yellow solid. 1H NMR (300 MHz, DMSO): δ 7.91-7.87 (m, 3H), 7.53-7.49 (m, 4 h), 6.54 (s, 1H), 4.43-4.40 (m, 1H), 2.08-2.06 (m, 4 h), 1.70 (s, 6H). LC-MS: [M+H]+, 293, tR=1.76 min, HPLC: 95% at 214 nm, 95.55% at 254 nm, tR=3.943 min.

Workup

customThe solvent was removed in vacuo
customthe resulting mixture was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=200:1)

Sources & evidence

ORD record: ord-3c3a89918f1647dd9196ae7e8f69c753
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169259B2

Reaction notes

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