1-(Bromomethyl)-2,4-difluorobenzene → HCID 57941498, compound

HRID 1437937Notes

Reaction equation

HRID 1437937 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]=[C:23]([F:25])[CH:22]=[CH:21][C:18]=1[CH2:19]Br>CN(C)C=O>[F:16][C:17]1[CH:24]=[C:23]([F:25])[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 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 57941341HCID 57941341, compound2×

Product 1

HCID 57941498HCID 57941498, compoundYield 51.4%

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 2,4-difluoro-benzyl bromide (62 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-(2,4-difluoro-benzyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (82 mg, 51%) as an off-white solid. APCI-MS (M+H) 333.

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-eaf9c935183a4a1c898e40fd069b3dbc
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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