1-(Bromomethyl)-4-(trifluoromethoxy)benzene → HCID 57941388, compound

HRID 1437945Notes

Reaction equation

HRID 1437945 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]([F:28])([F:27])[O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>CN(C)C=O>[F:16][C:17]([F:27])([F:28])[O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][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])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 57941341HCID 57941341, compound2×

Product 1

HCID 57941388HCID 57941388, compoundYield 60.2%

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 4-trifluoromethoxy-benzyl bromide (77 μL, 0.48 mmol) in N,N-dimethylformamide (5 mL) was heated at 100° C. overnight. 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-(4-trifluoromethoxy-benzyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (110 mg, 60%) as a light yellow oil. APCI-MS (M+H) 381.

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-7a11e912786b4fb89c46e914caffdc4f
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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