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Sodium Carbonate → N-(4-amino-5-cyano-6-phenylpyridin-2-yl)acetamide

HRID 1364525
ノート
印刷プレビュー

反応式

HRID 1364525 の反応式
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](Br)[N:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 11557905N-(4-Amino-6-bromo-5-cyano-pyridin-2-yl)-acetamide

生成物 1

HCID 11658882N-(4-amino-5-cyano-6-phenylpyridin-2-yl)acetamide収率 72.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 86606902
water THF DMF
溶媒

反応条件

温度
130 °C

実験手順

A mixture of bromide from Example 65A (45 mg, 0.18 mmol), Na2CO3 (38 mg, 0.35 mmol), and Pd(PPh3)4 (10 mg, 0.009 mmol) was stirred in DMF/THF/H2O (1:1:0.5) under nitrogen in a microwave reactor vial. Phenyl boric acid (26 mg, 0.21 mmol) was added. The resulting mixture was capped and heated at 130° C. for 20 min in a microwave reactor. The crude mixture was partitioned between EtOAc and water. The organic layer washed with water and brine, dried over Na2SO4, and evaporated under reduced pressure. The crude residue was purified by a Gilson reverse phase HPLC to provide the titled compound (33 mg, 72% yield). 1H NMR (300 MHz, d6-DMSO) δ 10.44 (s, 1H), 7.74-7.68 (m, 2H), 7.55 (s, 1H), 7.52-7.46 (m, 3H), 6.98 (s, 2H), 2.08 (s, 3H). MS (ESI) m/e 253 (M+H)+; m/e 251 (M−H)−.

後処理

  1. customThe resulting mixture was capped
  2. customThe crude mixture was partitioned between EtOAc and water
  3. washThe organic layer washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by a Gilson reverse phase HPLC

出典と根拠

ORDレコード
ord-5fa09abe9e974bc0b543db820b30e33e
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07888374B2

反応ノート

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