4-Formylphenylboronic Acid → HCID 57937848, 화합물

HRID 1435065노트

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HRID 1435065 반응식
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[CH:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13]>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=2[CH3:11])=[CH:16][CH:15]=1)=[O:13]

참가 물질

6

반응물 2

HCID 5910734-Formylphenylboronic AcidHCID 70208694-bromo-3-methylbenzamide

생성물 1

HCID 57937848HCID 57937848, 화합물수율 95.3%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

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온도
95 °C

실험 절차

4-Bromo-3-methyl-benzamide (15.02 g), 70 mmol), 4-formylphenylboronic acid (14.039, 91 mmol) and palladium tetrakis(triphenylphosphine) (5.03 g, 4 mmol) were combined in 1,2-dimethoxy ethane (5 ml) and 2M aqueous sodium carbonate (2.5 ml). After heating at 95° C. for 48 hours, the reaction mixture was cooled to ambient temperature and passed through a plug of Celite, rinsing with 1,2-dimethoxy ethane. The volatiles were removed under reduced pressure to yield 16 g of the title compound (I-4a) as a colorless solid.

후처리

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. washrinsing with 1,2-dimethoxy ethane
  3. customThe volatiles were removed under reduced pressure

출처 및 근거

ORD 기록
ord-b46535751b334f83a6a75da3e59ad255
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615651B2

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