Acetic Acid → 6-Iodo-2,3-dihydro-1H-indole

반응식

[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CC(O)=O>>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2

참가 물질

반응물 2

HCID 176Acetic Acid

HCID 27823135-Iodo-1H-indole

생성물 1

HCID 138639056-Iodo-2,3-dihydro-1H-indole수율 99.5%

실험 절차

To a solution of 5-iodoindole (0.2 g; 0.82 mmol) in AcOH (5 ml) NaBH3CN (0.2 g; 3.8 mmol) was added at ˜10° C. under N2. After stirring for 1 h at room temperature the solvent was removed in vacuo and the residue was diluted to 30 ml with Et2O and washed with 1 N NaOH (5 ml), H2O (2×5 ml), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound (0.2 g; 99%), which was used in next step without further purification. 1H-NMR (CDCl3) 7.35 (s, 1H); 7.25 (d, 1H, J=8.15 Hz); 6.43 (d, 1H, J=8.15 Hz); 5.21 (bs, 1H); 3.54 (t, 2H, J=8.36 Hz); 2.99 (t, 2H, J=8.36 Hz).

후처리

customwas removed in vacuo
additionthe residue was diluted to 30 ml with Et2O
washwashed with 1 N NaOH (5 ml), H2O (2×5 ml), brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customThe filtrate was evaporated to dryness under reduced pressure

출처 및 근거

ORD 기록: ord-0a3931f5cf5b430abc574827e2f5de2a
출처 데이터셋: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US09193716B2

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