1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → (2R)-N,N-Dibenzyl-8-(1-methyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 1099393Notes

Reaction equation

HRID 1099393 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.[CH2:16]([N:23]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@@H:24]1[CH2:33][CH2:32][C:31]2[C:26](=[C:27](Br)[CH:28]=[CH:29][CH:30]=2)[CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:35]([N:23]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:24]1[CH2:33][CH2:32][C:31]2[C:26](=[C:27]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:28]=[CH:29][CH:30]=2)[CH2:25]1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 22082960(2R)-N,N-dibenzyl-8-bromo-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 25114041(2R)-N,N-Dibenzyl-8-(1-methyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amineYield 96%

Procedure

The title compound was synthesized as described for Intermediate example I-2 in 96% yield, starting from 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole and (2R)-N,N-dibenzyl-8-bromo-1,2,3,4-tetrahydronaphthalen-2-amine: MS (ESI) m/z 408[M+H+].

Sources & evidence

ORD record
ord-f4994f76844d414d80635ebbb9fc3b21
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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