1-(Bromomethyl)-2-(trifluoromethyl)benzene → HCID 16118900, compound

HRID 1437935Notes

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:27])([F:26])[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br>CN(C)C=O>[CH3:1][N:2]1[C:10]2[C@@:9]3([CH3:14])[C:11]([CH3:12])([CH3:13])[C@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[N:3]1[CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=1[C:17]([F:16])([F:26])[F:27]

Participants

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-trifluoromethyl-benzyl bromide (77 μL, 0.51 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)-1,7,8,8-tetramethyl-2-(2-trifluoromethyl-benzyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (55.3 mg, 32%) as a light yellow solid. APCI-MS (M+H) 365.

Workup

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

Sources & evidence

ORD record: ord-e7f5d7dad0d548cfae049b50fda7f2d2
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622492B2

Reaction notes

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