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

HRID 1994192노트

반응식

HRID 1994192 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9277b8c30fda449fbac8eeb358589359
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652137B2

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