1,4-Dioxane → 2-(6-(4-(6-Fluoroindolin-1-yl)piperidin-1-yl)pyridazin-3-yl)-5-methylthiazole

HRID 512851Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([F:23])[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C[N:25]1[CH:29]=[CH:28][S:27][CH:26]1[Sn](CCCC)(CCCC)CCCC.O1CCOC[CH2:44]1>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>[F:23][C:20]1[CH:21]=[C:22]2[C:17]([CH2:16][CH2:15][N:14]2[CH:11]2[CH2:12][CH2:13][N:8]([C:5]3[N:6]=[N:7][C:2]([C:26]4[S:27][C:28]([CH3:44])=[CH:29][N:25]=4)=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a mixture of 1-(1-(6-chloropyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline (100 mg, 0.3 mmol) and Pd(PPh3)4 (35 mg, 0.03 mmol) was added 1,4-dioxane (2 mL) and then 3-methyl-2-tributylstannylthiazole (232 mg, 0.6 mmol). The resulting mixture was sealed and heated at 140° C. for 1.5 h. The resulting mixture was then absorbed on silica gel and purified by silica gel column using 40% EtOAc/hexane as the eluent to yield 2-(6-(4-(6-fluoroindolin-1-yl)piperidin-1-yl)pyridazin-3-yl)-5-methylthiazole.

Workup

customThe resulting mixture was sealed
customThe resulting mixture was then absorbed on silica gel
custompurified by silica gel column

Sources & evidence

ORD record: ord-d0cec945957846269df4decfa49b5a22
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102669B2

Reaction notes

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