Sodium Chlorite → 1H-Pyrrolo[2,3-B]pyridine-5-carboxylic acid, 1-[(1,1-dimethylethyl)dimethylsilyl]-

HRID 1994196노트

반응식

HRID 1994196 반응식
[C:1]([Si:5]([CH3:18])([CH3:17])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH:15]=[O:16])[CH:14]=[C:9]2[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].[O-:19]Cl=O.[Na+]>C(O)(C)(C)C.CC(=CC)C.O>[C:1]([Si:5]([CH3:18])([CH3:17])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([C:15]([OH:19])=[O:16])[CH:14]=[C:9]2[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 23668197Sodium ChloriteHCID 497590381H-Pyrrolo[2,3-B]pyridine-5-carboxaldehyde, 1-[(1,1-dimethylethyl)dimethylsilyl]-

생성물 1

HCID 497588951H-Pyrrolo[2,3-B]pyridine-5-carboxylic acid, 1-[(1,1-dimethylethyl)dimethylsilyl]-수율 16.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6386tert-Butanol용매HCID 105532-Methyl-2-butene용매

실험 절차

To a stirred and cooled (0° C.) solution of aldehyde 16 (115 mg, 0.44 mmol) in tert-butanol (3.1 mL) and 2-methyl-2-butene (0.77 mL) was added a solution of NaClO2 (194 mg, 2.1 mmol) and NaH2PO4.H2O (244 mg, 1.8 mmol) in water (2.31 mL) dropwise. When 16 was consumed (TLC) the mixture was partitioned between AcOEt and water. The organic layer was washed with saturated brine (1×), dried (MgSO4), filtered and concentrated to afford acid 11 (20 mg, 16%) as an off-white solid. 1H NMR (400 MHz; CDCl3) δ 0.66 (s, 6H), 0.94 (s, 9H), 6.65 (s, 1H), 7.32 (s, 1H), 8.61 (s, 1H) and 9.03 (s, 1H).

후처리

  1. customWhen 16 was consumed (TLC) the mixture
  2. customwas partitioned between AcOEt and water
  3. washThe organic layer was washed with saturated brine (1×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0b3dd40dc51649ba930d40f1ea995cc8
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652137B2

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