Cesium carbonate → HCID 59513720, compound

HRID 1160008Notes

Reaction equation

HRID 1160008 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:20]([C:21]3[C:26]([F:27])=[CH:25][N:24]=[C:23]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=4)[N:22]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[F:78][C:79]1[CH:87]=[CH:86][CH:85]=[C:84]([F:88])[C:80]=1[C:81]([NH2:83])=[O:82].C([O-])([O-])=O.[Cs+].[Cs+]>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>[F:78][C:79]1[CH:87]=[CH:86][CH:85]=[C:84]([F:88])[C:80]=1[C:81]([NH:83][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:20]([C:21]3[C:26]([F:27])=[CH:25][N:24]=[C:23]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=4)[N:22]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)[CH:3]=1)=[O:82]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 874392,6-DifluorobenzamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59513693HCID 59513693, compound

Product 1

HCID 59513720HCID 59513720, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To an oven-dried flask under N2 was added 4-[2-(3-bromophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]-5-fluoro-N-(3-fluorophenyl)-2-pyrimidinamine (40 mg, 0.08 mmol), anhydrous degassed 1,4-dioxane (10 mL), Pd2(dba)3 (13.4 mg, 0.01 mmol), Xantphos (12.7 mg, 0.02 mmol), 2,6-difluorobenzamide (34.5 mg, 0.2 mmol), and Cs2CO3 (83 mg, 0.26 mmol). The reaction was heated in the microwave at 160° C. for 15 min, adsorbed to silica gel, and purified by LC (DCM to 5% MeOH/DCM) to afford the desired product (30 mg, 66%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 6.63-6.67 (m, 1H), 7.10-7.25 (m, 4H), 7.29-7.34 (m, 2H), 7.39-7.47 (m, 1H), 7.53-7.59 (m, 1H), 7.68-7.70 (m, 2H), 8.04-8.10 (m, 2H), 8.60 (s, 1H), 9.57 (s, 1H), 9.97 (s, 1H), 10.87 (s, 1H); ESIMS (M+H)+=623.

Workup

  1. custompurified by LC (DCM to 5% MeOH/DCM)

Sources & evidence

ORD record
ord-fcea2cc23d20480abaa1801b0fc0d424
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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