Dichloromethane → HCID 86695287, compound

HRID 1057193Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12](/[C:16](/[C:35]3[CH:42]=[CH:41][C:38]([CH:39]=[O:40])=[CH:37][CH:36]=3)=[C:17](/[C:20]3[CH:25]=[CH:24][C:23](B4OC(C)(C)C(C)(C)O4)=[CH:22][CH:21]=3)\[CH2:18][CH3:19])=[CH:13][CH:14]=2)[CH:9]=[N:8]1.I[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1.[OH-].[K+].C(Cl)Cl>O1CCOCC1.C(OCC)(=O)C>[N:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=1[C:23]1[CH:22]=[CH:21][C:20](/[C:17](/[CH2:18][CH3:19])=[C:16](\[C:35]2[CH:42]=[CH:41][C:38]([CH:39]=[O:40])=[CH:37][CH:36]=2)/[C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[N:7]([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[N:8]=[CH:9]3)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (E)-4-(1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)but-1-en-1-yl)benzaldehyde (220 mg, 0.39 mmol), 2-iodopyridine (0.062 mL, 0.58 mmol), and KOH (6M aq., 0.40 mL, 2.34 mmol) in 1,4-dioxane was degassed with nitrogen. PdCl2dppf.DCM (31 mg, 0.04 mmol) was added and the resulting mixture was heated to 70° C. overnight. The mixture was cooled to room temperature and poured into ethyl acetate. The organic phase was washed with brine (3×), dried over sodium sulfate, and purified by flash chromatography on silica gel eluting with 0 to 50% ethyl acetate/hexanes to afford 82 mg of the title compound as a yellow foam. LCMS: 514 (M+H)+.

Workup

customwas degassed with nitrogen
temperatureThe mixture was cooled to room temperature
washThe organic phase was washed with brine (3×)
dry with materialdried over sodium sulfate
custompurified by flash chromatography on silica gel eluting with 0 to 50% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-df1b16d289d740c0ad63f4aed1a2c933
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399646B2

Reaction notes

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