Cesium carbonate → HCID 25218287, compound

HRID 2061899Notes

Reaction equation

HRID 2061899 reaction equation
[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9](Cl)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH:24]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[NH2:25].C([O-])([O-])=O.[Cs+].[Cs+]>>[C:1]([O:5][C:6]([C:7]1[CH:12]=[CH:11][C:10]2[C:9]([CH:8]=1)=[N:25][N:24]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[C:13]=2[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:22])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 223202584-Hydrazinylpyridine hydrochlorideHCID 67212057HCID 67212057, compound

Product 1

HCID 25218287HCID 25218287, compoundYield 54.3%

Procedure

The reaction was performed according to example 1 using 156.4 mg 3-chloro-4-phenylethynyl-benzoic acid tert-butyl ester, 101.9 mg 4-hydrazinopyridine hydrochloride (1.4 equiv.) and 456.2 mg Cs2CO3 (2.8 equiv.) with a reaction time of 2 hours at 110° C. This afforded 104.7 mg (54%) of the title compound. 1H-NMR (DMSO-d6) δ 1.58 (s, 9H), 4.66 (s, 2H), 6.98 (d, 2H, J=7.4 Hz), 7.15-7.24 (m, 3H), 7.51 (dd, 1H, J=8.8, 1.3 Hz), 7.69-7.73 (m, 3H), 8.30 (s, 1H), 8.77 (dd, 2H, J=4.6, 1.6 Hz); HRMS (FAB): Calculated for C24H24N3O2 (M+H+) 386.1869, found 386.1864.

Sources & evidence

ORD record
ord-74cbfc39cc614d93b8612fab4b705530
Source dataset
uspto-grants-2012_10
Patent number
US08283476B2

Reaction notes

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