N-bromobutanimide → 2-Amino-5-bromopyridine-4-carbonitrile

HRID 420490ノート

反応式

HRID 420490 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].C1C(=O)N([Br:17])C(=O)C1>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[C:4]([C:7]([Br:17])=[CH:8][N:9]=1)[C:5]#[N:6]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 70155242-Aminoisonicotinonitrile

生成物 1

HCID 534405772-Amino-5-bromopyridine-4-carbonitrile収率 78.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-18 °C

実験手順

A solution of 2-amino-isonicotinonitrile (10.0 g, 83.9 mmol) in DMF (20 mL) was cooled to −18° C. (ice/MeOH bath), treated with NBS (16.5 g, 92.3 mmol), and stirred at −18° C. for 1 h. The reaction mixture was diluted in AcOEt (500 mL) and washed with water (200 mL). The aqueous phase was separated and extracted with AcOEt (2×500 ml). The combined organic fractions were dried over Na2SO4, filtered and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 98:2→6:4) to yield the title compound (13.0 g, 65.6 mmol, 78%) as a pale yellow solid. MS: 199 [M+1]+; HPLC: AtRet=1.13; TLC: RF 0.39 (hexane/DCM/TBME 1:1:2).

後処理

  1. washwashed with water (200 mL)
  2. customThe aqueous phase was separated
  3. extractionextracted with AcOEt (2×500 ml)
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 98:2→6:4)

出典と根拠

ORDレコード
ord-18e64117c2b6408bab679b70265e2175
出典データセット
uspto-grants-2012_01
特許番号
US08097617B2

反応ノート

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