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tert-Butyl 2-(9-iodo-7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate → tert-Butyl 2-(7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 1964125
ノート
印刷プレビュー

反応式

HRID 1964125 の反応式
I[C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][CH:29]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:3]=12.[CH3:38][Zn]C>C1COCC1>[CH:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]3[N:4]4[CH2:27][CH2:28][CH:29]([CH2:30][C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[C:3]4=[C:2]([CH3:38])[C:10]=3[CH:9]=2)=[CH:14][C:15]=1[C:23]([F:26])([F:24])[F:25])([CH3:21])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 67251011tert-Butyl 2-(9-iodo-7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateHCID 178477796HCID 178477796、化合物

生成物 1

HCID 67249074tert-Butyl 2-(7-(4-Isopropoxy-3-(trifluoromethyl)benzyloxy)-9-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate収率 57.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 2-(9-iodo-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.778 g, 1.236 mmol) in THF (12.3 mL) under nitrogen was added 2 M solution of dimethylzinc (1.854 mL, 3.71 mmol), followed by bis(tri-t-butylphosphine)Pd(0) (0.057 g, 0.111 mmol). The reaction was stirred overnight, slowly quenched with saturated NaHCO3, diluted with EtOAc, and filtered through Celite®. The organics were washed with water (twice), brine, dried over MgSO4, and filtered. The solvent was removed under vacuum. The residue was purified by silica gel column chromatography to give the title compound as a solid (0.366 g). LCMS m/z=518.6 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.28 (d, J=5.94 Hz, 6H), 1.38 (s, 9H), 2.15 (s, 3H), 2.19-2.30 (m, 1H), 2.43-2.48 (m, 1H), 2.69-2.81 (m, 2H), 3.54-3.64 (m, 1H), 3.86-3.96 (m, 1H), 3.98-4.07 (m, 1H), 4.73-4.84 (m, 1H), 5.07 (s, 2H), 6.74 (dd, J=8.65, 2.34 Hz, 1H), 7.00 (d, J=2.27 Hz, 1H), 7.13 (d, J=8.72 Hz, 1H), 7.29 (d, J=9.35 Hz, 1H), 7.64-7.71 (m, 2H).

後処理

  1. customslowly quenched with saturated NaHCO3
  2. additiondiluted with EtOAc
  3. filtrationfiltered through Celite®
  4. washThe organics were washed with water (twice), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a1baa509f369487bb10a600e885635b4
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415484B2

反応ノート

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