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

HRID 1514176Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

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)+.

Workup

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

Sources & evidence

ORD record: ord-82bf89fe5c9f49afa4d085b51302de0d
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222245B2

Reaction notes

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