Lithium diisopropylamide → tert-butyl 3-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

HRID 2234065노트

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HRID 2234065 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.C(O[B:30]1[O:34][C:33]([CH3:36])([CH3:35])[C:32]([CH3:38])([CH3:37])[O:31]1)(C)C>O1CCCC1.C1COCC1.CCCCCC>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[C:9]1[B:30]1[O:34][C:33]([CH3:36])([CH3:35])[C:32]([CH3:38])([CH3:37])[O:31]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 2724682Lithium diisopropylamideHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 11806510tert-Butyl 3-methyl-1H-indole-1-carboxylate

생성물 1

HCID 67148908tert-butyl 3-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21883165Tetrahydrofuran hexane용매

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온도
0 °C

실험 절차

To a solution of 462 mg 3-methyl-indole-1-carboxylic acid tert-butyl ester in 2.5 ml anhydrous tetrahydrofuran at −78° C. under argon is 1.2 ml of a 2M LDA (Li-diisopropylamine) solution in THF/hexane and stirred at 0° C. for 30 min to complete the deprotonation. The reaction mixture is cooled to −78° C., 0.6 ml 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and stirred at 0° C. for 60 min. The reaction is quenched by the addition of 2 ml MeOH/water (1:1), diluted into water and extracted with ethylacetate. After evaporation of the solvent and purification on silica gel 385 mg of 3-methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester are obtained.

후처리

  1. customat −78° C.
  2. temperatureThe reaction mixture is cooled to −78° C.
  3. customThe reaction is quenched by the addition of 2 ml MeOH/water (1:1)
  4. additiondiluted into water
  5. extractionextracted with ethylacetate
  6. customAfter evaporation of the solvent and purification on silica gel 385 mg of 3-methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indole-1-carboxylic acid tert-butyl ester
  7. customare obtained

출처 및 근거

ORD 기록
ord-93513001838e49f28740aa253f3b1688
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709466B2

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