2-Furancarbonyl chloride → HCID 118080492, compound

HRID 1485702Notes

Reaction equation

HRID 1485702 reaction equation
O1C=CC=C1[C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[CH:23]=CC(S(C)(=O)=O)=C[CH:19]=3)[CH:16]=2)[NH:11][C@@H:10]([CH3:28])[CH2:9]1)=[O:7].O1C=C[CH:31]=[C:30]1C(Cl)=O.[CH:37]1([N:40]2C=C(B3OC(C)(C)C(C)(C)O3)C=[N:41]2)[CH2:39][CH2:38]1.CS(C1C=CC(B(O)O)=CC=1)(=O)=[O:56]>>[CH:37]1([N:40]2[CH:19]=[C:18]([C:15]3[CH:16]=[C:17]4[C:12]([NH:11][C@@H:10]([CH3:28])[CH2:9][N:8]4[C:6]([O:7][CH2:30][CH3:31])=[O:56])=[CH:13][CH:14]=3)[CH:23]=[N:41]2)[CH2:39][CH2:38]1

Participants

5

Reactant 4

HCID 682422-Furancarbonyl chlorideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 593271331-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 118079525HCID 118079525, compound

Product 1

HCID 118080492HCID 118080492, compound

Procedure

Ethyl (S)-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate was prepared according to the procedure outlined for (S)-furan-2-yl(3-methyl-7-(4-(methylsulfonyl)phenyl)-3,4-dihydroquinoxaline-1(2H)-yl)methanone, substituting ethyl chloroformate for furan-2-carbonyl chloride in Step 1 and 1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 4-(methylsulfonyl)phenylboronic acid in Step 2 to afford the desired product. MS (ESI, pos. ion) m/z 327 [M+1]+.

Workup

  1. customEthyl (S)-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate was prepared

Sources & evidence

ORD record
ord-3f72374e3bad49d1a773d1743a922d0b
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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