Iodoform → 7-Iodo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one

HRID 1514176

반응식

HRID 1514176 반응식
N[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1.[I:14]C(I)I.N(OC(C)(C)C)=O>C1COCC1>[I:14][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1

참가 물질

5

반응물 3

HCID 6374IodoformHCID 10906Tert-Butyl nitriteHCID 598623477-amino-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one

생성물 1

HCID 594034467-Iodo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one수율 67.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
50 °C

실험 절차

7-Amino-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (may be prepared as described in: Preparation of benzazepinylpyrrolidonylsulfonamides as Factor Xa inhibitors; WO2007059952) (500 mg, 2.84 mmol) and triiodomethane (2234 mg, 5.67 mmol) were dissolved in THF (100 ml). Then 1,1-dimethylethyl nitrite (0.675 ml, 5.67 mmol) dissolved in THF (20 ml) was added drop-wise over 20 minutes and the resultant solution stirred for 1 hour. The mixture was heated at 50° C. for 30 minutes. Most of the solvent was removed by evaporation and the crude subjected to biotage chromatography (EtOAc/hexane 3:1) to yield the title compound (550 mg) as a pale yellow solid. MS (ES) C10H10INO requires 287: found 287.8 (M+H)+.

후처리

  1. additionwas added drop-wise over 20 minutes
  2. customMost of the solvent was removed by evaporation

출처 및 근거

ORD 기록
ord-82bf89fe5c9f49afa4d085b51302de0d
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222245B2

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