3,5-Dimethylpyrazole-4-boronic acid, pinacol ester → (2R)-N,N-Dibenzyl-8-(3,5-dimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 1099394Notes

Reaction equation

HRID 1099394 reaction equation
[CH3:1][C:2]1[C:6](B2OC(C)(C)C(C)(C)O2)=[C:5]([CH3:16])[NH:4][N:3]=1.[CH2:17]([N:24]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C@@H:25]1[CH2:34][CH2:33][C:32]2[C:27](=[C:28](Br)[CH:29]=[CH:30][CH:31]=2)[CH2:26]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:36]([N:24]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:25]1[CH2:34][CH2:33][C:32]2[C:27](=[C:28]([C:6]3[C:2]([CH3:1])=[N:3][NH:4][C:5]=3[CH3:16])[CH:29]=[CH:30][CH:31]=2)[CH2:26]1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

3

Reactant 2

HCID 162177133,5-Dimethylpyrazole-4-boronic acid, pinacol esterHCID 22082960(2R)-N,N-dibenzyl-8-bromo-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 25114257(2R)-N,N-Dibenzyl-8-(3,5-dimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amineYield 58%

Procedure

The title compound was synthesized as described for Intermediate example I-4 in 58% yield, starting from 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1 H-pyrazole and (2R)-N,N-dibenzyl-8-bromo-1,2,3,4-tetrahydronaphthalen-2-amine (described in WO9905134A1): MS (ESI) m/z 422[M+H+].

Sources & evidence

ORD record
ord-a2c46af37fdc4cca9b59e6345cd5ad3a
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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