Cesium carbonate → Sodium (E)-2-((2Z,4E)-3-(3-(2-Carboxyethyl)phenyl)-5-(5-chloro-3,3-dimethyl-7-(3-sulfonatopropyl)-3H-pyrrolo[2,3-b]pyridin-7-ium-2-yl)penta-2,4-dienylidene)-3,3-dimethyl-1-(3-sulfonatopropyl)indoline-5-sulfonate

HRID 1425467Notes

Reaction equation

HRID 1425467 reaction equation
Br/[C:2](/[CH:27]=[CH:28]/[C:29]1[C:30]([CH3:47])([CH3:46])[C:31]2[C:32]([N:45]=1)=[N+:33]([CH2:38][CH2:39][CH2:40][S:41]([O-:44])(=[O:43])=[O:42])[CH:34]=[C:35]([Cl:37])[CH:36]=2)=[CH:3]\[CH:4]=[C:5]1\[N:6]([CH2:20][CH2:21][CH2:22][S:23]([O-:26])(=[O:25])=[O:24])[C:7]2[C:12]([C:13]\1([CH3:15])[CH3:14])=[CH:11][C:10]([S:16]([O-:19])(=[O:18])=[O:17])=[CH:9][CH:8]=2.[Na+:48].[Na+].[C:50]([CH2:53][CH2:54][C:55]1[CH:56]=[C:57](B(O)O)[CH:58]=[CH:59][CH:60]=1)([OH:52])=[O:51].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:50]([CH2:53][CH2:54][C:55]1[CH:56]=[C:57](/[C:2](/[CH:27]=[CH:28]/[C:29]2[C:30]([CH3:47])([CH3:46])[C:31]3[C:32]([N:45]=2)=[N+:33]([CH2:38][CH2:39][CH2:40][S:41]([O-:44])(=[O:43])=[O:42])[CH:34]=[C:35]([Cl:37])[CH:36]=3)=[CH:3]\[CH:4]=[C:5]2\[N:6]([CH2:20][CH2:21][CH2:22][S:23]([O-:26])(=[O:25])=[O:24])[C:7]3[C:12]([C:13]\2([CH3:15])[CH3:14])=[CH:11][C:10]([S:16]([O-:19])(=[O:17])=[O:18])=[CH:9][CH:8]=3)[CH:58]=[CH:59][CH:60]=1)([OH:52])=[O:51].[Na+:48].[Na+:48]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 38561183-(2-Carboxyethyl)phenylboronic acidHCID 86699468HCID 86699468, compound

Product 1

HCID 86699470Sodium (E)-2-((2Z,4E)-3-(3-(2-Carboxyethyl)phenyl)-5-(5-chloro-3,3-dimethyl-7-(3-sulfonatopropyl)-3H-pyrrolo[2,3-b]pyridin-7-ium-2-yl)penta-2,4-dienylidene)-3,3-dimethyl-1-(3-sulfonatopropyl)indoline-5-sulfonate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Compound 9 (80 mg), 3-(2-carboxyethyl)phenylboronic acid (40 mg), and cesium carbonate (20 mg) were stirred into water (20 mL) under nitrogen at room temperature. Tetrakis(triphenylphosphine)palladium (0) (10 mg) were added to the reaction mixture. The mixture was refluxed for 4 h, and the solvent and volatile compounds then were evaporated under vacuum. The crude product was purified by flash chromatography on silica 60, 200-400 mesh, eluting with a 20/80 acetonitrile/water mixture. The purified compound 56 had λMeOH=680 nm, λPBS=672 nm, ε=160,000. The absorption and emission data is shown in Table 2 and FIG. 1.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. customthe solvent and volatile compounds then were evaporated under vacuum
  3. customThe crude product was purified by flash chromatography on silica 60, 200-400 mesh
  4. washeluting with a 20/80 acetonitrile/water mixture
  5. customThe absorption and emission data

Sources & evidence

ORD record
ord-dd4c8d76000448a6a1d3ed0d6027fcfc
Source dataset
uspto-grants-2015_01
Patent number
US08927719B2

Reaction notes

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