alpha-Bromo-o-fluorotoluene → HCID 86695589, compound

HRID 1465723Notes

Reaction equation

HRID 1465723 reaction equation
[C@H:1]12[NH:8][C@H:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH:2]2[C:9]([O:11][CH3:12])=[O:10].[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][N:8]1[C@@H:5]2[CH2:6][CH2:7][C@H:1]1[CH:2]([C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:4]2

Participants

5

Reactant 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 81531DiisopropylethylamineHCID 86695588HCID 86695588, compound

Product 1

HCID 86695589HCID 86695589, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (1S,5S)-methyl 8-azabicyclo[3.2.1]octane-2-carboxylate (185 mg, 1.1 mmol) dissolved in DCM (11 mL) was added 2-fluorobenzylbromide (206 mg, 1.1 mmol), followed by N,N-diisopropylethylamine (424 mg, 3.3 mmol). After stirring for 1 hour, the reaction mixture was quenched with water, and extracted with DCM. Dried and concentrated to give 186 mg of crude product. The crude was carried over the next step without further purification.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with DCM
  3. customDried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1999b18e0993453ca65f0c1a07f1564f
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

Loading…