alpha-Bromo-o-fluorotoluene → HCID 16116866, compound

HRID 1437938Notes

Reaction equation

HRID 1437938 reaction equation
[CH3:1][N:2]1[C:10]2[C@@:9]3([CH3:14])[C:11]([CH3:13])([CH3:12])[C@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[NH:3]1.[F:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Br>CN(C)C=O>[F:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][N:3]1[C:4](=[O:15])[C:5]2[C@@H:6]3[C:11]([CH3:12])([CH3:13])[C@@:9]([CH3:14])([CH2:8][CH2:7]3)[C:10]=2[N:2]1[CH3:1]

Participants

4

Reactant 2

HCID 67968alpha-Bromo-o-fluorotolueneHCID 57941341HCID 57941341, compound2×

Product 1

HCID 16116866HCID 16116866, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.49 mmol) and 2-fluoro-benzyl bromide (58 μL, 0.48 mmol) in N,N-dimethylformamide (5 mL) was heated at 100° C. overnight and then allowed to stand at room temperature for five days. The reaction mixture was evaporated and the residue was purified using a Biotage 40S system, eluting with 0-1% methanol/chloroform, followed by drying under high vacuum to give (4S,7R)-2-(2-fluoro-benzyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (63 mg, 42%) as a white solid. APCI-MS (M+H) 315.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified
  3. washeluting with 0-1% methanol/chloroform
  4. customby drying under high vacuum

Sources & evidence

ORD record
ord-53a17d17b44449a8a7a7b5d83f3440a5
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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