Potassium Carbonate → HCID 57530509, compound

HRID 1454458Notes

Reaction equation

Cl[C:2]1[C:3]2[CH:24]=[CH:23][C:22](=[O:25])[N:21]([C:26]3[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=3[F:33])[C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[N:7]=1.[CH3:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][C:36]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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:32][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([F:33])[C:26]=1[N:21]1[C:4]2[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][CH:11]([N:14]4[CH2:19][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15]4)[CH2:10][CH2:9]3)[N:7]=[C:2]([C:36]3[CH:37]=[C:38]([CH:42]=[CH:43][C:35]=3[CH3:34])[C:39]([OH:41])=[O:40])[C:3]=2[CH:24]=[CH:23][C:22]1=[O:25]

Participants

Conditions

Temperature: 150 °C

Procedure

To the compound 4-chloro-8-(2,6-difluorophenyl)-2-(4-methyl-1,4′-bipiperidin-1′-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (47.5 mg, 0.1 mmol) in dioxane (3 mL) and water (1 mL) were added 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (38.4 mg, 0.15 mol), potassium carbonate (83 mg, 0.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (4.6 mL, 0.005 mmol). The mixture was heated with microwave at about 150° C. for about 15 min. The mixture was concentrated & then mixed with DMSO (0.75 mL) and water (0.25 mL). Separation by HPLC afforded the title compound (39 mg, 68%). LC-MS m/z 574 (M+H)+.

Workup

concentrationThe mixture was concentrated
additionmixed with DMSO (0.75 mL) and water (0.25 mL)
customSeparation by HPLC

Sources & evidence

ORD record: ord-514e4a26441e40b2873fa6835c5724e0
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07479558B2

Reaction notes

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