(2,4-Dimethylphenyl)boronic acid → N-(3,4-dihydro-2H-chromen-4-yl)-5-(2,4-dimethylphenyl)-3,6-diethylpyrazin-2-amine

HRID 1824125Notes

Reaction equation

HRID 1824125 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].[CH3:52][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>[O:43]1[C:44]2[C:49](=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:40]([NH:39][C:34]2[C:33]([CH2:50][CH3:51])=[N:32][C:31]([C:54]3[CH:55]=[CH:56][C:57]([CH3:59])=[CH:58][C:53]=3[CH3:52])=[C:36]([CH2:37][CH3:38])[N:35]=2)[CH2:41][CH2:42]1

Participants

6

Reactant 3

HCID 4198739(2,4-Dimethylphenyl)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 10215966N-(3,4-dihydro-2H-chromen-4-yl)-5-(2,4-dimethylphenyl)-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, 2,4-dimethyl 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) 7.38, 7.22, 7.11–6.90, 5.38, 4.58, 4.31, 2.68, 2.53, 2.37, 2.26, 2.14, 1.25–1.15; HRMS (FAB) calcd for C25H29N3O+H 388.2389, found 388.2383.

Sources & evidence

ORD record
ord-28004423594542da88beadfb069f2dd4
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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