تفاعل #1135846

معادلة التفاعل

Lithium aluminum hydride

5-iodo-N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxamide

→

5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde

المردود 90.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىwas continued at 0° C. until the reaction
2. 2
   أخرىThe reaction was quenched by the slow addition of EtOAc at 0° C.
3. 3
   workup.ADDITIONthe whole mixture was poured into 0.4 N NaHSO4
4. 4
   غسيلThe organic layer was washed with brine
5. 5
   تجفيفdried over MgSO4
6. 6
   تركيزconcentrated
7. 7
   أخرىpurified on a silica gel column (100% EtOAc→3:97 MeOH:DCM)

الإجراء التجريبي

Lithium aluminum hydride (160 mg, 4.21 mmol) was added in portions to a cooled (0° C.) solution of 5-iodo-N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxamide (XI) (1.46 g, 3.5 mmol) in THF. Stirring was continued at 0° C. until the reaction was completed, approximately 30 min. The reaction was quenched by the slow addition of EtOAc at 0° C., and the whole mixture was poured into 0.4 N NaHSO4. The organic layer was washed with brine, dried over MgSO4, concentrated, and purified on a silica gel column (100% EtOAc→3:97 MeOH:DCM) to give 5-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde (I) as a white solid (0.90 g, 3.15 mmol, 72% yield). 1H NMR (DMSO-d6) δ ppm 1.50-1.71 (m, 2H), 1.71-1.87 (m, 1H), 1.97-2.15 (m, 2H), 2.31-2.42 (m, 1H), 3.66-3.99 (m, 2H), 5.96-6.17 (m, 1H), 7.78 (d, J=6 Hz, 1H), 7.84 (d, J=6 Hz, 1H), 8.50 (s, 1H), 10.13 (s, 1H); ESIMS found for C13H13IN2O2 m/z 357 (M+H).

المصدر