Dimethylformamide → 1-(tert-Butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 1994192ノート

反応式

HRID 1994192 の反応式
Br[C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C:5]2=[N:6][CH:7]=1.C([Li])(C)(C)C.CCCCC.CN([CH:31]=[O:32])C>CCOCC>[C:14]([Si:11]([CH3:13])([CH3:12])[N:8]1[C:5]2=[N:6][CH:7]=[C:2]([CH:31]=[O:32])[CH:3]=[C:4]2[CH2:10][CH2:9]1)([CH3:17])([CH3:16])[CH3:15]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8003PentaneHCID 587309295-Bromo-1-(tert-butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridineHCID 178418306HCID 178418306、化合物

生成物 1

HCID 587309341-(tert-Butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde収率 103.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a stirred and cooled (−78° C.) solution of the bromide 4 (5.00 g, 15.96 mmol) in Et2O (92 mL) was added dropwise 1.5 M solution of tert-butyllithium in pentane (22.3 mL, 33.5 mmol). After 45 min additional stirring at −78° C., DMF (5.6 mL, 72.3 mmol) was added dropwise, and the mixture was allowed to slowly warm to r.t. After 20 h the mixture was partitioned between saturated aqueous NaHCO3 solution and CH2Cl2. The organic layer was separated, dried (MgSO4), and concentrated to afford the crude aldehyde 13 (4.32 g). 1H NMR (400 MHz; CDCl3) δ 0.32 (s, 6H), 0.92 (s, 9H), 3.02 (m, 2H), 3.70 (m, 2H), 7.55 (d, J=2.0 Hz, 1H), 8.16 (d, J=2.0 Hz, 1H), 9.61 (s, 1H).

後処理

  1. stirringAfter 45 min additional stirring at −78° C.
  2. customAfter 20 h the mixture was partitioned between saturated aqueous NaHCO3 solution and CH2Cl2
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-9277b8c30fda449fbac8eeb358589359
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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