Methyl iodide → 3-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1-methyl-1H-indole

HRID 1768016노트

반응식

HRID 1768016 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][N:12]2[CH2:17][CH:16]=[C:15]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:14][CH2:13]2)=[CH:2]1.[CH3:27]CCCCC.CI>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][N:12]2[CH2:13][CH:14]=[C:15]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH3:27])[CH:19]=3)[CH2:16][CH2:17]2)=[CH:2]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 8058HexaneHCID 112336643-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole

생성물 1

HCID 117490943-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1-methyl-1H-indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole (358 mg, 1 mmol) (obtained from example 29, step 2) in dry THF (50 ml) was slowly added to a stirred suspension of hexane and washed with 60% sodium hydride (44 mg) at 0° C. After the addition, the reaction mixture was stirred for 30 min and methyl iodide (213 mg, 1.5 mmol) was added. The reaction mixture was stirred for 4 hrs and quenched carefully with ice cold water. The reaction mixture was extracted with chloroform; washed well with water; dried over anhydrous MgSO4; filtered and concentrated. The residue obtained was purified by silica-gel column chromatography by eluting it with 50% ethyl acetate:hexane. Light green semi-solid. Yield: 98 mg (26%); 373 (M+H); 1HNMR (400 MHz, CDCl3): 8.08˜7.82 (m, 3H); 7.40˜6.90 (m, 7H); 6.21˜6.19 (s, 1H); 3.80 (s, 3H); 3.48˜2.60 (m, 10H).

후처리

  1. washwashed with 60% sodium hydride (44 mg) at 0° C
  2. additionAfter the addition
  3. stirringThe reaction mixture was stirred for 4 hrs
  4. customquenched carefully with ice cold water
  5. extractionThe reaction mixture was extracted with chloroform
  6. washwashed well with water
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue obtained
  11. customwas purified by silica-gel column chromatography
  12. washby eluting it with 50% ethyl acetate

출처 및 근거

ORD 기록
ord-5fcec68228f14c1389f0803f3b5f2ba0
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235569B2

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