Potassium Phosphate, Tribasic → Ethyl 2-(3-bromo-5-phenylthiophen-2-yl)-2-(tert-butoxy)acetate

HRID 590987노트

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HRID 590987 반응식
[C:1]([O:5][CH:6]([C:12]1[S:13][C:14](Br)=[CH:15][C:16]=1[Br:17])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Br:17][C:16]1[CH:15]=[C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[S:13][C:12]=1[CH:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 70819068Ethyl 2-(tert-butoxy)-2-(3,5-dibromothiophen-2-yl)acetate

생성물 1

HCID 70819430Ethyl 2-(3-bromo-5-phenylthiophen-2-yl)-2-(tert-butoxy)acetate수율 65%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 8028Tetrahydrofuran용매2회

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온도
60 °C

실험 절차

To a solution of ethyl 2-(tert-butoxy)-2-(3,5-dibromothiophen-2-yl)acetate (10c) (70 mg, 0.17 mmol) in tetrahydrofuran (1 mL) were added tripotassium phosphate (111 mg, 0.52 mmol), phenylboronic acid (23 mg, 0.19 mmol) and a solution of palladium acetate (1.2 mg, 5.2 μmol) and xantphos (3.0 mg, 5.2 μmol) in tetrahydrofuran (1 mL) previously stirred for 5 minutes. The reaction mixture was heated at 60° C. for 3 hours. The mixture was then filtered and the precipitate was rinsed with dichloromethane (5 mL). The filtrate was concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane/ethyl acetate 80/20) to provide the desired product (10d) (45 mg, 0.11 mmol, 65%).

후처리

  1. filtrationThe mixture was then filtered
  2. washthe precipitate was rinsed with dichloromethane (5 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (cyclohexane/ethyl acetate 80/20)

출처 및 근거

ORD 기록
ord-32173e6a3ae54120bc11d7ca52c6b78c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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