Cesium carbonate → HCID 89429084, compound

HRID 527191Notes

Reaction equation

[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[C:27](=[O:28])[NH:26][N:25]=[CH:24]4)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.BrC1C=CC(S(O[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][N:46]=[N+:47]=[N-:48])(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[N:46]([CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][N:26]1[C:27](=[O:28])[N:23]([C:20]2[CH:21]=[CH:22][C:17]([N:14]3[CH2:13][CH2:12][N:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=4)[CH2:16][CH2:15]3)=[CH:18][CH:19]=2)[CH:24]=[N:25]1)=[N+:47]=[N-:48]

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 56593708HCID 56593708, compound

HCID 89428897HCID 89428897, compound

Product 1

HCID 89429084HCID 89429084, compoundYield 62%

Procedure

This compound was synthesized as a yellowish amorphous solid from 13 (114.4 mg, 0.30 mmol), 3p (130.4 mg, 0.36 mmol), and Cs2CO3 (146.6 mg, 0.45 mmol) in 62% yield by following general procedure 1.2: 1H NMR (400 MHz, CDCl3, δH) 7.61 (s, 1H), 7.41 (d, J=9.0 Hz, 2H), 7.08-6.93 (m, 6H), 5.13 (s, 2H), 3.85 (t, J=7.1 Hz, 2H), 3.48 (s, 3H), 3.41-3.33 (m, 4H), 3.31-3.22 (m, 6H), 1.88-1.74 (m, 2H), 1.61 (dt, J=14.0, 7.0 Hz, 2H), 1.52-1.35 (m, 4H). ESI-MS: 507.3 (M+H+), 529.3 (M+Na+).

Sources & evidence

ORD record: ord-26ad628ff10048fd8cd3e8746f83f4ab
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346791B2

Reaction notes

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