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

HRID 2251106ノート

反応式

HRID 2251106 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9bd59b94ecfd4449b1a3226cd6fa03fa
出典データセット
uspto-grants-2008_01
特許番号
US07319103B2

反応ノート

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