Water → 2-{[3-(Azidomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile

HRID 1874920ノート

反応式

HRID 1874920 の反応式
Br[CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[C:13]([Cl:19])[N:12]=2)[C:6]([Cl:9])=[CH:7][CH:8]=1.[N-:21]=[N+:22]=[N-:23].[Na+].O.C([O-])(O)=O.[Na+]>CS(C)=O>[N:21]([CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[C:13]([Cl:19])[N:12]=2)[C:6]([Cl:9])=[CH:7][CH:8]=1)=[N+:22]=[N-:23]

参加物

6

反応物 4

HCID 962WaterHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 86644895HCID 86644895、化合物

生成物 1

HCID 866448962-{[3-(Azidomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile収率 98%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
25 °C

実験手順

2-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (2.00 g, 5.32 mmol) and sodium azide (0.346 g, 5.32 mmol) were combined in DMSO (10 mL) and stirred 16 h at 25° C. at which time TLC indicated complete conversion (10% Et2O/hexanes). Water (150 mL) and saturated aqueous NaHCO3 (30 mL) were added and the mixture stirred vigorously for 30 min. The resultant precipitate was filtered off, washed with water, and air dried to give 2-{[3-(azidomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (1.76 g, 5.21 mmol, 98% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.01 (d, J=0.73 Hz, 1H), 7.96 (d, J=0.73 Hz, 1H), 7.48-7.60 (m, 2H), 4.60 (s, 2H).

後処理

  1. stirringthe mixture stirred vigorously for 30 min
  2. filtrationThe resultant precipitate was filtered off
  3. washwashed with water, and air
  4. customdried

出典と根拠

ORDレコード
ord-20e0dab825194fd2a9fa74c82d6ee2c2
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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