Dichloromethane → HCID 178511587, compound

HRID 1963850Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)[CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[N:18]=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.CO.CS(C)=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].C(O)C.COCCOC>[F:16][C:17]1[N:18]=[C:19]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]3[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]3)[CH:3]=2)[CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of trans-N1-(4-bromopyridin-2-yl)cyclohexane-1,4-diamine (102 mg, 0.377 mmol), 2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (80 mg, 0.359 mmol), PdCl2(dppf).CH2Cl2 adduct (29.3 mg, 0.036 mmol), DME (2 ml), Ethanol (0.2 ml), and 2M sodium carbonate (0.717 ml, 1.435 mmol) reaction mixture was stirred at about 85° C. until completion, as indicated by LCMS. The crude mixture was cooled to room temperature, diluted with 5 ml of ethyl acetate and 2 ml of methanol, filtered and concentrated to yield a crude solid. The solid was dissolved in DMSO, refiltered, purified by prep LC, and lyophilized to yield 64 mg of the title compound as its TFA salt. LCMS (m/z): 287.2 (MH+), retention time=0.43 min.

Workup

filtrationfiltered
concentrationconcentrated
customto yield a crude solid
custompurified by prep LC

Sources & evidence

ORD record: ord-748d45dba1884acc95c7743908a86b55
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415381B2

Reaction notes

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