Diiodomethane → HCID 135730591, compound

HRID 354195Notes

Reaction equation

N(OCCCC)=O.[Br:8][C:9]1[N:10]([CH3:29])[N:11]=[C:12]2[C:17](=[O:18])[NH:16][C:15]([C:19]3[C:20]([O:26][CH2:27][CH3:28])=[N:21][CH:22]=[C:23](N)[CH:24]=3)=[N:14][C:13]=12.[I:30]CI>>[Br:8][C:9]1[N:10]([CH3:29])[N:11]=[C:12]2[C:17](=[O:18])[NH:16][C:15]([C:19]3[C:20]([O:26][CH2:27][CH3:28])=[N:21][CH:22]=[C:23]([I:30])[CH:24]=3)=[N:14][C:13]=12

Participants

Reactant 3

HCID 6346Diiodomethane

HCID 10996Butyl nitrite

HCID 135730621HCID 135730621, compound

Product 1

HCID 135730591HCID 135730591, compoundYield 23%

Conditions

Temperature: 45 °C

Procedure

Butyl nitrite (282 mg, 2.74 mmol) was added dropwise to a stirred suspension of the title compound of Example 54 (200 mg, 0.55 mmol) in diiodomethane (2 mL) at room temperature. After 1 h the reaction was warmed for 2 h at 40-50° C. The mixture was cooled and purified directly by flash column chromatography (gradient elution from dichloromethane to 98% dichloromethane/5% methanol) to give the product as a brown solid (60 mg, 23%).

Workup

temperatureThe mixture was cooled
custompurified directly by flash column chromatography (gradient elution from dichloromethane to 98% dichloromethane/5% methanol)

Sources & evidence

ORD record: ord-f06e2fcb881d483695058ffe04412dac
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756373B1

Reaction notes

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