Cesium carbonate → HCID 25218292, compound

HRID 2061901Notes

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.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][NH:30][NH2:31].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:31][N:30]([CH2:29][C:25]1[S:24][CH:28]=[CH:27][CH:26]=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

Reactant 3

HCID 10796Cesium carbonate

HCID 67212057HCID 67212057, compound

HCID 67212177(2-Thienylmethyl)hydrazine hydrochloride

Product 1

HCID 25218292HCID 25218292, compoundYield 36%

Procedure

The reaction was performed according to example 1 using 156.4 mg 3-chloro-4-phenylethynyl-benzoic acid tert-butyl ester, 164.7 mg thiophen-2-ylmethyl-hydrazine hydrochloride (2.0 equiv.) and 488.7 mg Cs2CO3 (3.0 equiv.) with a reaction time of 5 hours at 110° C. This afforded 72.8 mg (36%) of the title compound. 1H-NMR (DMSO-d6) δ 1.56 (s, 9H), 4.58 (s, 2H), 5.86 (s, 2H), 6.93 (dd, 1H, J=5.1, 3.5 Hz), 7.04 (dd, 1H, J=3.5, 1.0 Hz), 7.16 (d, 2H, J=7.4 Hz), 7.20-7.29 (m, 3H), 7.42 (dd, 1H, J=8.8, 1.2 Hz), 7.44 (dd, 1H, J=5.0, 1.2 Hz), 7.55 (dd, 1H, J=8.7, 0.7 Hz), 8.20 (s, 1H).

Sources & evidence

ORD record: ord-307f5b5bc443418aa4c0cb04b5c9921a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283476B2

Reaction notes

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