Chloroform → HCID 66988923, compound

HRID 1944890Notes

Reaction equation

HRID 1944890 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]3[C:18](=[C:19]([CH3:21])[CH:20]=2)[N:17]=[CH:16][C:15]([C:22]([NH2:24])=[O:23])=[C:14]3[NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[OH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)(Cl)Cl>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([C:11]3[CH:12]=[C:13]4[C:18](=[C:19]([CH3:21])[CH:20]=3)[N:17]=[CH:16][C:15]([C:22]([NH2:24])=[O:23])=[C:14]4[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)(=[O:10])=[O:9])[CH:3]=2)=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 669882606-((3-Bromophenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

Product 1

HCID 66988923HCID 66988923, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of Intermediate 62 (0.95 mmol) and 4-(hydroxymethyl)phenylboronic acid (290 mg, 1.90 mmol) in DME (10 mL) at room temperature was added 2 M Na2CO3 (1.4 mL, 2.85 mmol) and PdCl2(PPh3)2 (33 mg, 0.005 mmol). The reaction mixture was stirred at reflux for 2 h and then cooled to room temperature. After the addition of 60 mL of chloroform, a white precipitate formed which was collected by filtration. The crude product was purified by flash column chromatography (0-15% MeOH in dichloromethane) to give the title compound (357 mg, 68% for 3 steps). ES/MS calcd. for C31H28N3O5S+ 554.2. Found m/z=554.3 (M+H)+.

Workup

  1. temperatureat reflux for 2 h
  2. customa white precipitate formed which
  3. filtrationwas collected by filtration
  4. customThe crude product was purified by flash column chromatography (0-15% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-fdb110c740ee49648ddd3c1ba0af73e0
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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