Di-tert-butyl dicarbonate → Tert-butyl(6-bromo-3-methoxypyridin-2-yl)carbamate

HRID 1772885노트

반응식

HRID 1772885 반응식
BrC1N=C(N)C(OC)=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[C:26]([O:30][C:31]([N:33]([C:41]1[C:46]([O:47][CH3:48])=[CH:45][CH:44]=[C:43]([Br:49])[N:42]=1)C(OC(C)(C)C)=O)=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C)C1C=CN=CC=1.CC#N>[C:26]([O:30][C:31](=[O:32])[NH:33][C:41]1[C:46]([O:47][CH3:48])=[CH:45][CH:44]=[C:43]([Br:49])[N:42]=1)([CH3:29])([CH3:27])[CH3:28]

참가 물질

6

반응물 3

HCID 90495Di-tert-butyl dicarbonateHCID 575629062-Amino-6-bromo-3-methoxypyridineHCID 118685198Di-tert-butyl(6-bromo-3-methoxypyridin-2-yl)imidodicarbonate

생성물 1

HCID 131734688Tert-butyl(6-bromo-3-methoxypyridin-2-yl)carbamate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매

실험 절차

A mixture of 6-bromo-3-methoxypyridin-2-amine (10.2 g, 50.2 mmol), Boc2O (38.2 g, 0.18 mol) and 4-(dimethylamino)pyridine (1.2 g, 9.82 mmol) in MeCN (550 mL) was refluxed for 2 h. After cooling to rt and concentration in vacuo EtOAc (500 mL) was added and the organic phase washed with water (100 mL) and brine (50 mL). The organic phase was dried (MgSO4), filtered and the filtrate concentrated in vacuo. Purification by chromatography eluting with 4:1 DCM-heptane yielded a mixture of the title compound and di-tert-butyl(6-bromo-3-methoxypyridin-2-yl)imidodicarbonate (10.6 g) in an approximate ratio of 55:45.

후처리

  1. temperaturewas refluxed for 2 h
  2. concentrationconcentration in vacuo EtOAc (500 mL)
  3. additionwas added
  4. washthe organic phase washed with water (100 mL) and brine (50 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification by chromatography
  9. washeluting with 4:1 DCM-heptane
  10. customyielded

출처 및 근거

ORD 기록
ord-0c5f5d9864ed461fa7bcf07e8b4192b3
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249160B2

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