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 1425467노트

반응식

HRID 1425467 반응식
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]

참가 물질

6

반응물 3

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

생성물 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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dd4c8d76000448a6a1d3ed0d6027fcfc
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927719B2

반응 노트

불러오는 중…