tert-Butanol → 2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-5-carboxylic acid

HRID 381766

반응식

HRID 381766 반응식
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:19]1[C:20](=[O:29])[NH:21]C2C(C=1)=CC=CC=2)=O)(C)(C)C.[CH3:30][C:31]([CH2:33][CH3:34])=[CH2:32].OP([O-])(O)=O.[Na+].Cl([O-])=[O:42].[Na+].[CH3:45][C:46](O)(C)C>C1COCC1>[O:29]=[C:20]1[C:19]([C:9]2[NH:8][C:16]3[C:11]([CH:10]=2)=[CH:12][C:13]([C:17]([OH:18])=[O:42])=[CH:14][CH:15]=3)=[CH:30][C:31]2[C:32](=[CH:45][CH:46]=[CH:34][CH:33]=2)[NH:21]1

참가 물질

7

반응물 5

HCID 6386tert-ButanolHCID 112402-Methyl-1-buteneHCID 121116895-Formyl-2-(2-oxo-1,2-dihydro-quinolin-3-yl)-indole-1-carboxylic acid tert-butyl esterHCID 23668197Sodium Chlorite2회HCID 23672064Monosodium phosphate2회

생성물 1

HCID 226682542-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-5-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-(2-oxo-1,2-dihydro-3-quinolinyl)i1H-indole-5-carbaldehyde (5-8, 500 mg, 1.29 mmol, 1 equiv) in a 4:1 mixture of THF and t-BuOH was treated with 2 -methyl butene (8 mL), an aqueous solution of sodium phosphate monobasic (0.14 M 355.2 mg, 2.57 mmol, 2.00 equiv), and sodium chlorite (232.8 mg, 2.57 mmol, 2.00 equiv). Additional solid sodium phosphate monobasic (380 mg, 2.76 mmol, 2.14 equiv) and sodium chlorite (300 mg, 3.32 mmol, 2.57 equiv) was added in 2 equal portions over 2.5 h. The reaction mixture was concentrated, and the residue dissolved in EtOAc (60 mL), then washed twice with a 25:1 mixture of aqueous 10% sodium bisulfite solution and 10% potassium hydrogen sulfate solution (2×50 mL). The organic layer was dried over sodium sulfate, concentrated, and combined with a precipitate in the aqueous layer which was filtered and dried to 2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-5-carboxylic acid (6-1) as an off-white solid. 1H NMR (500 MHz, DMSO) δ12.13 (s, 1H), 8.27 (s, 1H), 8.14 (m, 3H), 7.95 (d, 1H, J=7.8 Hz), 7.76 (d, 1H, J=7.8 Hz), 7.54 (t, 1H, J=7.8), 7.36 (d, 1H, J=7.8), 7.24 (t, 1H, J=7.8) 1.36 (s, 9H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in EtOAc (60 mL)
  3. washwashed twice with a 25:1 mixture of aqueous 10% sodium bisulfite solution and 10% potassium hydrogen sulfate solution (2×50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. filtrationwas filtered
  7. dry with materialdried to 2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-5-carboxylic acid (6-1) as an off-white solid

출처 및 근거

ORD 기록
ord-34b9e7618b89497b8757735dccc7a32d
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306874B1

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