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

HRID 1994196ノート

反応式

HRID 1994196 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 105532-Methyl-2-butene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0b3dd40dc51649ba930d40f1ea995cc8
出典データセット
uspto-grants-2010_01
特許番号
US07652137B2

反応ノート

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