Water → Sodium 2-((1E,3Z,5E)-3-(3-(4-Carboxybutyl)phenyl)-5-(1,1-dimethyl-6,8-disulfonato-3-(3-sulfonatopropyl)-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dienyl)-1,1-dimethyl-3-(3-sulfonatopropyl)-1H-benzo[e]indolium-6,8-disulfonate

HRID 449535Notes

Reaction equation

HRID 449535 reaction equation
Br/[C:2](=[CH:35]\[CH:36]=[C:37]1\[N:38]([CH2:60][CH2:61][CH2:62][S:63]([O-:66])(=[O:65])=[O:64])[C:39]2[CH:40]=[CH:41][C:42]3[C:51]([S:52]([O-:55])(=[O:54])=[O:53])=[CH:50][C:49]([S:56]([O-:59])(=[O:58])=[O:57])=[CH:48][C:43]=3[C:44]=2[C:45]\1([CH3:47])[CH3:46])/[CH:3]=[CH:4]/[C:5]1[C:13]([CH3:15])([CH3:14])[C:12]2[C:11]3[CH:16]=[C:17]([S:24]([O-:27])(=[O:26])=[O:25])[CH:18]=[C:19]([S:20]([O-:23])(=[O:22])=[O:21])[C:10]=3[CH:9]=[CH:8][C:7]=2[N+:6]=1[CH2:28][CH2:29][CH2:30][S:31]([O-:34])(=[O:33])=[O:32].[Na+:67].[Na+].[Na+].[Na+].[Na+].[C:72]([CH2:75][CH2:76][CH2:77][CH2:78][C:79]1[CH:80]=[C:81](B(O)O)[CH:82]=[CH:83][CH:84]=1)([OH:74])=[O:73].C(=O)([O-])[O-].[Cs+].[Cs+].O>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.C(O)C>[C:72]([CH2:75][CH2:76][CH2:77][CH2:78][C:79]1[CH:80]=[C:81](/[C:2](=[CH:35]\[CH:36]=[C:37]2\[N:38]([CH2:60][CH2:61][CH2:62][S:63]([O-:66])(=[O:65])=[O:64])[C:39]3[CH:40]=[CH:41][C:42]4[C:51]([S:52]([O-:55])(=[O:54])=[O:53])=[CH:50][C:49]([S:56]([O-:59])(=[O:57])=[O:58])=[CH:48][C:43]=4[C:44]=3[C:45]\2([CH3:47])[CH3:46])/[CH:3]=[CH:4]/[C:5]2[C:13]([CH3:14])([CH3:15])[C:12]3[C:11]4[CH:16]=[C:17]([S:24]([O-:27])(=[O:25])=[O:26])[CH:18]=[C:19]([S:20]([O-:23])(=[O:21])=[O:22])[C:10]=4[CH:9]=[CH:8][C:7]=3[N+:6]=2[CH2:28][CH2:29][CH2:30][S:31]([O-:34])(=[O:32])=[O:33])[CH:82]=[CH:83][CH:84]=1)([OH:74])=[O:73].[Na+:67].[Na+:67].[Na+:67].[Na+:67].[Na+:67]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 467389575-(3-Boronophenyl)pentanoic acidHCID 86649203Sodium 2-((1E,3Z,5E)-3-Bromo-5-(1,1-dimethyl-6,8-disulfonato-3-(3-sulfonatopropyl)-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dienyl)-1,1-dimethyl-3-(3-sulfonatopropyl)-1H-benzo[e]indolium-6,8-disulfonate

Product 1

HCID 86649207Sodium 2-((1E,3Z,5E)-3-(3-(4-Carboxybutyl)phenyl)-5-(1,1-dimethyl-6,8-disulfonato-3-(3-sulfonatopropyl)-1H-benzo[e]indol-2(3H)-ylidene)penta-1,3-dienyl)-1,1-dimethyl-3-(3-sulfonatopropyl)-1H-benzo[e]indolium-6,8-disulfonate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Compound 6 (80 mg), 3-(4-carboxybutyl)phenylboronic acid (40 mg), and cesium carbonate (20 mg) are stirred into 1:1 water:ethanol (10 ml) under nitrogen at room temperature. Tetrakis(triphenylphosphine)palladium(0) (10 mg) is added to the reaction mixture. The mixture was refluxed for 4 hours, and the solvent and volatile compounds are evaporated under vacuum. The crude product is purified by flash chromatography on reverse-phase C18-functionalized silica by eluting with a 1:4 acetonitrile:water mixture. The purified product 8 has UV/vis absorption max of λMeOH=680 nm, ε=229,000; λPBS676 nm, ε=239,000.

Workup

  1. customat room temperature
  2. temperatureThe mixture was refluxed for 4 hours
  3. customthe solvent and volatile compounds are evaporated under vacuum
  4. customThe crude product is purified by flash chromatography on reverse-phase C18-functionalized silica
  5. washby eluting with a 1:4 acetonitrile
  6. customUV/vis absorption max of λMeOH=680 nm, ε=229,000

Sources & evidence

ORD record
ord-e580f60a63104e9b81a2a32dac8f6b67
Source dataset
uspto-grants-2013_07
Patent number
US08481752B2

Reaction notes

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