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1,2-Dichloroethane → 2-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

HRID 1623743
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HRID 1623743 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:13]([CH:17]=1)[C:14](O)=[O:15].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:13]([CH:17]=1)[C:14]([NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:15]
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참가 물질

6

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HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 24613572-(Benzyloxy)-5-bromobenzoic acid

생성물 1

HCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
20 °C

실험 절차

3-Pyridinamine (123 mg, 1.30 mmol) in DCM (15 ml) was added to a stirred solution of 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method A; 200 mg, 0.65 mmol), HOBT (150 mg, 0.98 mmol) and EDC (187 mg, 0.98 mmol) in DCM (15 ml) under nitrogen at room temperature. The reaction mixture was stirred at 20° C. overnight. The reaction mixture was partitioned between DCM (50 ml) and water (25 ml). The organic phase was washed with saturated brine (25 ml), dried over sodium sulphate and evaporated in vacuo to give the crude product as a yellow solid. The crude product was added to a Biotage column and was eluted with petroleum ether:ethyl acetate (3:1) to yield the title compound as a white solid. 75 mg. MS (electrospray): m/z [M+H]+=383

후처리

  1. customThe reaction mixture was partitioned between DCM (50 ml) and water (25 ml)
  2. washThe organic phase was washed with saturated brine (25 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo
  5. customto give the crude product as a yellow solid
  6. washwas eluted with petroleum ether:ethyl acetate (3:1)

출처 및 근거

ORD 기록
ord-e34d7c7f7cae46e0aced29d4eb3a589a
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778939B2

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