4-Fluoro-2-(trifluoromethyl)benzyl bromide → HCID 57941424, compound

HRID 1437944Notes

Reaction equation

HRID 1437944 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][C:20]([CH2:21]Br)=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=1>CN(C)C=O>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:3]2[C:4](=[O:15])[C:5]3[C@@H:6]4[C:11]([CH3:12])([CH3:13])[C@@:9]([CH3:14])([CH2:8][CH2:7]4)[C:10]=3[N:2]2[CH3:1])=[C:19]([C:25]([F:26])([F:27])[F:28])[CH:18]=1

Participants

4

Reactant 2

HCID 27375764-Fluoro-2-(trifluoromethyl)benzyl bromideHCID 57941341HCID 57941341, compound2×

Product 1

HCID 57941424HCID 57941424, compoundYield 55.1%

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; 210 mg, 1.02 mmol) and 4-fluoro-2-trifluoromethyl-benzyl bromide (470 μL, 3.04 mmol) in N,N-dimethylformamide (10 mL) was heated at 100° C. overnight. The reaction mixture was evaporated and the residue was purified using a Biotage 40M system, eluting with 0-0.5% methanol/chloroform, followed by drying under high vacuum to give (4S,7R)-2-(4-fluoro-2-trifluoromethyl-benzyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (215 mg, 55%) as an off-white solid. APCI-MS (M+H) 383.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified
  3. washeluting with 0-0.5% methanol/chloroform
  4. customby drying under high vacuum

Sources & evidence

ORD record
ord-472a975b12cf496d9031ce4bcacc3eb6
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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