Dichloromethane → HCID 86596186, compound

HRID 2108531Notes

Reaction equation

HRID 2108531 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14](Cl)[C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[CH2:21](Br)[CH:22]=[CH2:23].C1CCN2C(=NCCC2)CC1.[Cl:36]CCl>CCOC(C)=O>[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][C:10]([Cl:36])([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH2:21][CH:22]=[CH2:23])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7841Allyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22292779HCID 22292779, compound

Product 1

HCID 86596186HCID 86596186, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-trifluoroacetyl-8-chloro-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (24 mg, 0.078 mmol) in dichloromethane (2 mL) was treated with allyl bromide (18 mg, 0.15 mmol), DBU (23 mg, 0.15 mmol) and stirred 2 hours at 20 C. The product mixture was diluted with EtOAc (10 mL), washed with 5% aqueous HCl (5 mL), brine (5 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 23 mg of a white solid. MS calculated for C16H17ClF3NO2+H: 348, observed: 348.

Workup

  1. washwashed with 5% aqueous HCl (5 mL), brine (5 mL)
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cdfdeceb1db349cdbc5767b0bf71e5c5
Source dataset
uspto-grants-2009_04
Patent number
US07514422B2

Reaction notes

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