Water → 5-Chloro-4-methyl-3-nitropyridine-2-carboxaldehyde

HRID 2062029

반응식

HRID 2062029 반응식
N[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[C:5]([Cl:12])=[CH:4][N:3]=1.Br[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[C:18]([CH3:23])[C:17]([Cl:24])=[CH:16][N:15]=1.I([O-])(=O)(=O)=O.[Na+].[OH2:31]>C1COCC1.[Os](=O)(=O)(=O)=O>[Cl:12][C:5]1[C:6]([CH3:11])=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([CH:14]=[O:31])=[N:3][CH:4]=1.[Cl:24][C:17]1[C:18]([CH3:23])=[C:19]([N+:20]([O-:22])=[O:21])[C:14]([CH:2]=[CH2:7])=[N:15][CH:16]=1

참가 물질

8

반응물 4

HCID 962Water2회HCID 214641365-Chloro-4-methyl-3-nitropyridin-2-amineHCID 23667635Sodium periodateHCID 866255962-Bromo-5-chloro-4-methyl-3-nitropyridine

생성물 2

HCID 666198835-Chloro-4-methyl-3-nitro-2-vinylpyridineHCID 866255955-Chloro-4-methyl-3-nitropyridine-2-carboxaldehyde수율 56%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

2-Amino-3-(6-chloro-3-methoxy-7-methyl-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropionitrile (26 mg) was prepared using a procedure similar to that described in Example 1, part b, except starting from 1-(6-chloro-3-methoxy-7-methyl-2H-pyrazolo[4,3-b]pyridin-2-yl)propan-2-one (78 mg). 1-(6-Chloro-3-methoxy-7-methyl-2H-pyrazolo[4,3-b]pyridin-2-yl)propan-2-one was prepared using a procedure similar to that described in Example 105 part a to d except using 5-chloro-4-methyl-3-nitropyridine-2-carboxaldehyde (1.3 g) in part a to yield [2-(tert-butyldimethylsilanyloxy)propyl]-(5-chloro-4-methyl-3-nitropyridin-2-yl-methyl)amine (1.4 g, 57%). 5-Chloro-4-methyl-3-nitro-pyridine-2-carboxaldehyde was prepared using a procedure similar to that described in Example 136 part a to c except starting from 2-amino-5-chloro-4-methyl-3-nitropyridine (32 g) in part a to generate 2-bromo-5-chloro-4-methyl-3-nitropyridine (25.2 g, 59%). Oxidative cleavage using a 4% solution of osmium tetroxide in water (1.5 mL) and sodium periodate (2.5 g) was carried out in a mixture of THF and water (10:1, 60 mL) in part c instead of ozonolysis following a procedure similar to that described in Example 61 to afford 5-chloro-4-methyl-3-nitropyridine-2-carboxaldehyde (1.3 g, 56%) from 5-chloro-4-methyl-3-nitro-2-vinylpyridine (2.3 g). 2-Amino-5-chloro-4-methyl-3-nitropyridine (4.6 g, 75%) was prepared using a procedure similar to that described in Example 38 part a except starting from 2-amino-4-methyl-3-nitropyridine (5 g) and using N-chlorosuccinimide (5.8 g) instead of N-bromosuccinimide.

후처리

  1. custom5-Chloro-4-methyl-3-nitro-pyridine-2-carboxaldehyde was prepared

출처 및 근거

ORD 기록
ord-5752df5f6b0a4a1a9d6b327c88d9acfe
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283475B2

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