Cesium carbonate → HCID 71272247, compound

HRID 1771850Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=[C:10]2[NH:18][C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH:20][C:9]=12.[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]([CH3:41])[S:37]([CH3:40])(=[O:39])=[O:38])#[CH:29]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[NH:18][C:10]3=[N:11][CH:12]=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]([C:29]#[C:28][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[N:36]([CH3:41])[S:37]([CH3:40])(=[O:39])=[O:38])=[C:9]3[CH:20]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Cul (19 mg), Pd(OAc)2 (22 mg) and Cs2CO3 (1.27 g) are added to a degassed solution of 4-chloro-2-(4-fluorophenyl)-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]-pyridine (628 mg), N-(2-ethynylphenyl)-N-methylmethanesulfonamide (450 mg) in 1,4-dioxane (10 ml), and the mixture is stirred at 100° C. for 5 h. Conventional work-up and purification gives the title compound in 70% yield (663 mg).

Workup

customConventional work-up and purification

Sources & evidence

ORD record: ord-d8b0e72f0f0948bb9db017eaab54b538
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249140B2

Reaction notes

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