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

HRID 1772885ノート

反応式

HRID 1772885 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0c5f5d9864ed461fa7bcf07e8b4192b3
出典データセット
uspto-grants-2016_02
特許番号
US09249160B2

反応ノート

読み込み中…