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 1425467ノート

反応式

HRID 1425467 の反応式
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]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 38561183-(2-Carboxyethyl)phenylboronic acidHCID 86699468HCID 86699468、化合物

生成物 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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dd4c8d76000448a6a1d3ed0d6027fcfc
出典データセット
uspto-grants-2015_01
特許番号
US08927719B2

反応ノート

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