1-Bromo-3-chloropropane → 10-[4-(3-chloro-propoxy)-phenyl]-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene

HRID 2251106노트

반응식

HRID 2251106 반응식
[N:1]1[N:9]2[C:4]([N:5]=[C:6]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:7]3=[C:8]2[C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:3][CH:2]=1.Br[CH2:23][CH2:24][CH2:25][Cl:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Cl:26][CH2:25][CH2:24][CH2:23][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[N:9]3[C:4]([N:5]=[C:6]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:7]=24)=[CH:3][CH:2]=[N:1]3)=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1360572464-(6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]inden-10-yl)-phenol

생성물 1

HCID 5858770610-[4-(3-chloro-propoxy)-phenyl]-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene수율 32%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of 4-(6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]inden-10-yl)-phenol (60 mg, 0.2 mmol) in DMF (1 mL) was added 1-bromo-3-chloropropane (67 mg, 0.4 mol) and K2CO3 (45 mg, 0.3 mmol). The mixture was stirred at 80° C. for 5 hours, then cooled, diluted with EtOAc (3 mL) and washed with H2O. The organic layer was washed with brine, dried over MgSO4, and concentrated. The residue was purified via preparative LCMS to give 10-[4-(3-chloro-propoxy)-phenyl]-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene (13 mg, 32% yield).

후처리

  1. temperaturecooled
  2. washwashed with H2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified via preparative LCMS

출처 및 근거

ORD 기록
ord-9bd59b94ecfd4449b1a3226cd6fa03fa
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07319103B2

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