2-Iodo-3-methoxypyridine → 4-(3-Methoxypyridin-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 532813노트

반응식

HRID 532813 반응식
I[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10]([N:17]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].CC(C)([O-])C.[Na+]>C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C1(C)C=CC=CC=1>[C:13]([O:12][C:10]([N:17]1[CH2:23][CH2:22][CH2:21][N:20]([C:2]2[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:19][CH2:18]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

참가 물질

6

반응물 3

HCID 8171732-Iodo-3-methoxypyridineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 23676156Sodium t-butoxide

생성물 1

HCID 593662084-(3-Methoxypyridin-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl촉매HCID 1140Toluene용매

반응 조건

온도
65 °C

실험 절차

Toluene (1.5 mL) was added to a mixture of 2-iodo-3-methoxypyridine (350 mg, 1.49 mmol), BOC-homopiperazine (0.410 mL, 2.09 mL), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (26 mg, 0.07 mmol), and trisdibenzylideneacetone dipalladium (20 mg, 0.02 mmol). To this suspension was added sodium t-butoxide (201 mg, 2.09 mmol) and the mixture was heated to 65° C. for 15 h. The mixture was filtered through celite, and the filter cake was washed with EtOAc. The resulting solution was washed with H2O, then brine, and dried over MgSO4. After removal of the solvent, the residue was purified on silica to give 335 mg of the title compound as a dark oil. MS (ES) m/z 308 (M+H+).

후처리

  1. filtrationThe mixture was filtered through celite
  2. washthe filter cake was washed with EtOAc
  3. washThe resulting solution was washed with H2O
  4. dry with materialbrine, and dried over MgSO4
  5. customAfter removal of the solvent
  6. customthe residue was purified on silica

출처 및 근거

ORD 기록
ord-c19f8b2708c24170a3db4ad51240f2e4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853202B2

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