Potassium Phosphate, Tribasic → HCID 53329360, compound

HRID 1029009Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9]1.[O:17]1[CH2:22][CH2:21][N:20]([C:23]2[C:24]([NH2:42])=[N:25][C:26]3[C:31]([CH:32]=2)=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][CH:27]=3)[CH2:19][CH2:18]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1>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]>[N:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:29]2[CH:30]=[C:31]3[C:26](=[CH:27][CH:28]=2)[N:25]=[C:24]([NH2:42])[C:23]([N:20]2[CH2:19][CH2:18][O:17][CH2:22][CH2:21]2)=[CH:32]3)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 1-(2-iodophenyl)-1H-indazole (0.18 g, 0.563 mmol), 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.10 g, 0.282 mmol, prepared as in Example 2, Step 1-2), potassium phosphate tribasic (0.12 mL, 1.408 mmol), Pd2(dba)3 (0.026 g, 0.028 mmol), and 2-(dicyclohexylphosphino)-2′,4′,6′,-tri-1-propyl-1,1′-biphenyl (0.027 g, 0.056 mmol) in dioxane/water (3/1.5 mL) was heated in mw for 12 min at 140° C. The mixture was concentrated and chromatographed on silica gel using 0-5% 2M NH3 MeOH/DCM to afford a light yellow oil which was repurified by HPLC to afford a white solid as 6-(2-(1H-indazol-1-yl)phenyl)-3-morpholinoquinolin-2-amine. MS (ESI, pos. ion) m/z: 422 (M+1).

Workup

concentrationThe mixture was concentrated
customchromatographed on silica gel using 0-5% 2M NH3 MeOH/DCM
customto afford a light yellow oil which
customwas repurified by HPLC

Sources & evidence

ORD record: ord-ce82102eb1ee47b19b3d37a3bc419906
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735384B2

Reaction notes

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