Bromoacetonitrile → HCID 86637602, 화합물

HRID 1694371노트

반응식

HRID 1694371 반응식
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH2:13]([O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24]Br)[N:19]=1)=[O:17])[CH3:14].Br[CH2:27][C:28]#[N:29].[NH4+].[Cl-]>CS(C)=O>[CH2:13]([O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:10][C:9]2[CH:8]=[CH:7][CH:6]=[C:3]([CH:4]=[O:5])[C:2]=2[O:1][CH2:27][C:28]#[N:29])[N:19]=1)=[O:17])[CH3:14]

참가 물질

7

반응물 5

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 905792,3-DihydroxybenzaldehydeHCID 23033755Ethyl 6-(bromomethyl)picolinate

생성물 1

HCID 86637602HCID 86637602, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To 2,3-dihydroxybenzaldehyde (1 mmol) in dry DMSO (2.5 mL) is added NaH (60% suspension in oil, 2.5 mmol). After 10 minutes, 6-bromomethyl-pyridine-2-carboxylic acid ethyl ester (1 mmol) is added. After 1 hour, bromoacetonitrile (0.07 mL, 1 mmol) is introduced at ambient temperature and mixture is stirred for 16 hours. Saturated aqueous NH4Cl solution is used to quench the reaction and the mixture is extracted with EtOAc. After drying over sodium sulfate, solvent is removed. Purification of the mixture by preparative HPLC (20-70% MeCN/H2O) gives 6-(2-cyanomethoxy-3-formyl-phenoxymethyl)-pyridine-2-carboxylic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ 10.4 (s, 1H), 8.1 (d, J=7.7 Hz, 1H), 7.9 (t, J=7.9 Hz, 1H), 7.7 (d, J=8.2 Hz, 1H), 7.5 (dd, J=8.2, 2.4 Hz, 1H), 7.24 (m, 2H), 5.42 (s, 2H), 5.14 (s, 2H), 4.5 (q, J=7.2 Hz, 2H), 1.45 (t, J=7 Hz, 3H); LC/MS (ES+): 341.2 (M+1)+.

후처리

  1. waitAfter 1 hour
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture is extracted with EtOAc
  5. dry with materialAfter drying over sodium sulfate, solvent
  6. customis removed
  7. customPurification of the mixture by preparative HPLC (20-70% MeCN/H2O)

출처 및 근거

ORD 기록
ord-3799c70c8dc344b48c8943dcf21c5527
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158662B2

반응 노트

불러오는 중…