Tetrahydrofuran → Methyl 2-amino-5-methoxy-3-methylbenzoate

HRID 249919노트

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HRID 249919 반응식
[NH2:1][C:2]1C(OC)=CC(Br)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CB(O)O.[F-].[K+].[C:21]([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:1][C:2]1[C:35]([CH3:21])=[CH:34][C:38]([O:37][CH3:36])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

7

반응물 5

HCID 8028TetrahydrofuranHCID 139377Methylboronic AcidHCID 522689Potassium FluorideHCID 4060964Tri-t-butylphosphoniumHCID 13894022Methyl 2-amino-5-bromo-3-methoxybenzoate

생성물 1

HCID 20281873Methyl 2-amino-5-methoxy-3-methylbenzoate수율 73%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
70 °C

실험 절차

A mixture of methyl 2-amino-5-bromo-3-methoxybenzoate (6.50 g, 25 mmol), methylboronic acid (3.0 g, 50 mmol), potassium fluoride (5.8 g, 100 mmol) and tri-t-butylphosphonium tetrafluoroborte (0.87 g, 3.0 mmol) in THF (200 mL) was deoxygenated and then backfilled with argon. Tris(dibenzylideneacetone)dipalladium(0) (1.43 g, 1.5 mmol), was added and the mixture was heated at 70° C. for 17 h under an argon atmosphere. The reaction mixture was concentrated and the residue purified by column chromatography (silica gel, 0% to 5% EtOAc in hexanes) to afford methyl 2-amino-5-methoxy-3-methylbenzoate (3.55 g, 73%) 1H NMR consistent.

후처리

  1. customwas deoxygenated
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue purified by column chromatography (silica gel, 0% to 5% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-35df134f9a174ac298eb7dd43559fd3c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863271B2

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