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

HRID 1364525
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HRID 1364525 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 86606902
water THF DMF
용매

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온도
130 °C

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-5fa09abe9e974bc0b543db820b30e33e
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07888374B2

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