Potassium Phosphate, Tribasic → HCID 67458007, compound

HRID 1853031Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:22][C:23]#[N:24])[CH2:16][N:15]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:14]3)[CH:12]=2)[N:5]2[CH:25]=[CH:26][N:27]=[C:4]2[CH:3]=1.[CH2:28]([N:30]1[CH:34]=[C:33](B(O)O)[CH:32]=[N:31]1)[CH3:29].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>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].O1CCOCC1>[CH2:28]([N:30]1[CH:34]=[C:33]([C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[N:10][N:11]([C:13]4([CH2:22][C:23]#[N:24])[CH2:14][N:15]([CH2:17][C:18]([F:21])([F:19])[F:20])[CH2:16]4)[CH:12]=3)[N:5]3[CH:25]=[CH:26][N:27]=[C:4]3[CH:3]=2)[CH:32]=[N:31]1)[CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

In a flask containing 2-(3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-(2,2,2-trifluoroethyl)azetidin-3-yl)acetonitrile (0.015 g, 0.038 mmol), 1-ethyl-1H-pyrazol-4-ylboronic acid (0.0080 g, 0.057 mmol), and K3PO4 (0.057 mL, 0.11 mmol) was added 1 mL of dioxane and argon was bubbled through for 10 minutes before dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.0036 g, 0.0076 mmol) and tris(dibenzylideneacetone)dipalladium (0.0035 g, 0.0038 mmol) were added and the reaction was then sealed and heated to 80° C. for 6 hours. The reaction mixture was loaded directly onto a silica gel column and eluted with EtOAc containing 0.5% NH4OH to afford the title compound (0.015 g, 0.031 mmol, 83% yield). MS (apci) m/z=456.2 (M+H).

Workup

additionwere added
customthe reaction was then sealed
washeluted with EtOAc containing 0.5% NH4OH

Sources & evidence

ORD record: ord-0ae7e6495cc64480a9104168e330229b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

Loading…