(2-Chloro-4-methylphenyl)boronic acid → 5-(2-chloro-4-methylphenyl)-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine

HRID 1612210Notes

Reaction equation

HRID 1612210 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1CC.Br[C:31]1[N:32]=[C:33]([CH2:50][CH3:51])[C:34]([NH:39][CH:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[O:43][CH2:42][CH2:41]2)=[N:35][C:36]=1[CH2:37][CH3:38].[Cl:52][C:53]1[CH:58]=[C:57]([CH3:59])[CH:56]=[CH:55][C:54]=1B(O)O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[Cl:52][C:53]1[CH:58]=[C:57]([CH3:59])[CH:56]=[CH:55][C:54]=1[C:31]1[N:32]=[C:33]([CH2:50][CH3:51])[C:34]([NH:39][CH:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[O:43][CH2:42][CH2:41]2)=[N:35][C:36]=1[CH2:37][CH3:38]

Participants

6

Reactant 3

HCID 2773334(2-Chloro-4-methylphenyl)boronic acidHCID 221472675-bromo-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amineHCID 58583246(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 102377955-(2-chloro-4-methylphenyl)-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Following the procedure for the preparation of (1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol but substituting 5-bromo-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine, ethylene glycol dimethyl ether, 2-chloro-4-methyl phenyl boronic acid and tetrakis(triphenylphosphine) palladium and making non-critical variations provided the title compound as a oil: 1H NMR (300 MHz, CDCl3) δ) 7.37-7.13, 6.99-6.90, 5.37, 4.64, 4.31, 2.69, 2.54, 2.40, 2.30, 1.29-1.17; HRMS (FAB) calcd for C24H26ClN3O+H 408.1842, found 408.1848. Anal. Calcd for C24H26ClN3O: C, 70.66; H, 6.42; N, 10.30. Found: C, 70.93; H, 6.78; N, 10.01.

Sources & evidence

ORD record
ord-2a5576a25b4d434e86c41123c169ec87
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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