4-Iodobenzyl bromide → HCID 69020890, compound

HRID 1437960Notes

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.[I:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1>CN(C)C=O>[I: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])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (4R,7S)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 104 mg, 0.50 mmol) and 4-iodo-benzyl bromide (163.5 mg, 0.55 mmol) in N,N-dimethylformamide (5 mL) was heated at 80° C. over the weekend and then allowed to stand at room temperature for three 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 (4R,7S)-2-(4-iodo-benzyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (144 mg, 68%) as an off-white solid. APCI-MS (M+H) 423.

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-8c8b297e7acf4a1ca60691a8ddf8eb5c
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622492B2

Reaction notes

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