Acetic Acid → 4-[2-(5-Bromo-pyridin-2-ylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester

HRID 2401115노트

반응식

HRID 2401115 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.ClC(Cl)C.[CH3:13][O:14][C:15]([C:17]1([CH2:23][CH:24]=O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:13][O:14][C:15]([C:17]1([CH2:23][CH2:24][NH:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)=[O:16]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 706222-Amino-5-bromopyridineHCID 5049666Sodium triacetoxyborohydrideHCID 58468045methyl 4-(2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate

생성물 1

HCID 674786784-[2-(5-Bromo-pyridin-2-ylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 5-bromopyridin-2-amine (0.488 g, 2.82 mmol) in 1-2 dichloroethane (DCE, 10 mL) was added desired 4-(2-oxo-ethyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (0.529 g, 2.82), acetic acid (3.1 eq) and allowed to stir at room temperature for an hour. NaBH(OAc)3 (3 eq) was then added in one portion and reaction mixture allowed to stir at room temperature for 16 hours. The reaction mixture was then diluted with DCM (10 mL), quenched with 2 M of NH4OH in water. The aqueous layer was extracted with DCM (10 mL×2). The combined organic layers were washed with aqueous NaHCO3 (30 mL), brine (30 mL), and dried over Na2SO4, and concentrated under vacuum.

후처리

  1. stirringto stir at room temperature for 16 hours
  2. customquenched with 2 M of NH4OH in water
  3. extractionThe aqueous layer was extracted with DCM (10 mL×2)
  4. washThe combined organic layers were washed with aqueous NaHCO3 (30 mL), brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-1ce9037896ae4782af7e7b40aefd4a15
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796278B2

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