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Triisopropyl borate → 1-cyclopentyl-5-fluoro-3-(methoxycarbonyl)-6-methyl-1H-indol-2-ylboronic acid

HRID 1028021
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HRID 1028021 반응식
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][C:11]([F:16])=[C:12]([CH3:15])[CH:13]=3)[C:8]([C:17]([O:19][CH3:20])=[O:18])=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:24][B:25](OC(C)C)[O:26]C(C)C)(C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][C:11]([F:16])=[C:12]([CH3:15])[CH:13]=3)[C:8]([C:17]([O:19][CH3:20])=[O:18])=[C:7]2[B:25]([OH:26])[OH:24])[CH2:2][CH2:3][CH2:4][CH2:5]1
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참가 물질

5

반응물 3

HCID 21531Triisopropyl borateHCID 2724682Lithium diisopropylamideHCID 66730594methyl 1-cyclopentyl-5-fluoro-6-methyl-1H-indole-3-carboxylate

생성물 1

HCID 667309151-cyclopentyl-5-fluoro-3-(methoxycarbonyl)-6-methyl-1H-indol-2-ylboronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Into a solution of methyl 1-cyclopentyl-5-fluoro-6-methyl-1H-indole-3-carboxylate (2.64 g, 9.6 mmol) and triisopropylborate (4.0 mL, 17.28 mmol) in THF (40 mL) at −78° C. was added LDA (1.5 M, 8.3 mL, 12.48 mmol) dropwise. The mixture was stirred for 45 min, and then treated with ice water and extracted with dichloromethane. The organic layer was dried over sodium sulfate and evaporated to give 1-cyclopentyl-5-fluoro-3-(methoxycarbonyl)-6-methyl-1H-indol-2-ylboronic acid as a semi-solid (3.1 g, ˜50% pure), which was used in next step without further purification.

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated

출처 및 근거

ORD 기록
ord-1a285fa56851494c99890dcea37afbda
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08735414B2

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