Oxalyl chloride → 4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide

HRID 245661노트

반응식

HRID 245661 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:13]([OH:15])=O)[N:7]2[CH3:12].C(Cl)(=O)C(Cl)=O.COC1C=CC=C2C=1C=C(C(Cl)=O)N2C.[NH2:37][C:38]1[CH:43]=[CH:42][C:41]([B:44]2[O:52][C:49]([CH3:51])([CH3:50])[C:46]([CH3:48])([CH3:47])[O:45]2)=[CH:40][C:39]=1[O:53][CH3:54]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.ClCCl.Cl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:13]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([B:44]3[O:45][C:46]([CH3:47])([CH3:48])[C:49]([CH3:51])([CH3:50])[O:52]3)=[CH:40][C:39]=1[O:53][CH3:54])=[O:15])[N:7]2[CH3:12]

참가 물질

10

반응물 4

HCID 65578Oxalyl chlorideHCID 31595784-Methoxy-1-methyl-1H-indole-2-carboxylic acidHCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 866746604-methoxy-1-methyl-1H-indole-2-carbonyl chloride

생성물 1

HCID 673656514-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide수율 99.9%

시약·촉매·용매 5

HCID 6344Dichloromethane촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 313Hydrochloric Acid용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

To 4-methoxy-1-methyl-1H-indole-2-carboxylic acid (24.4 mmol, 5 g) and oxalyl chloride (24.4 mmol, 2.3 mL) in dichloromethane (60 mL) N,N-dimethylformamide (1.22 mmol, 95 μL) was added and the mixture was stirred at room temperature until it formed a clear solution (approximately 4 hours). The mixture was concentrated in vacuo. The residue, 4-methoxy-1-methyl-1H-indole-2-carbonyl chloride, was added to a solution of 4-amino-3-methoxyphenylboronic acid pinacol ester (24.2 mmol, 6.03 g) and 4-dimethylaminopyridine (2.419 mmol, 0.296 g) in pyridine (30 mL) and dichloromethane (30 mL). After stirring at room temperature overnight the reaction mixture was diluted with dichloromethane and 2N hydrochloric acid. The organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic layers were dried (sodium sulfate) and concentrated in vacuo to yield 10.55 g of the title compound.

후처리

  1. customformed a clear solution (approximately 4 hours)
  2. concentrationThe mixture was concentrated in vacuo
  3. stirringAfter stirring at room temperature overnight the reaction mixture
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with dichloromethane
  6. dry with materialThe combined organic layers were dried (sodium sulfate)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ea2a8a69d0844001ab4f721623d537d3
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

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