2-(2-(Acetoxymethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one → HCID 58044223, compound

HRID 1918929Notes

Reaction equation

HRID 1918929 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH:16]3[CH2:19][N:18]([CH3:20])[CH2:17]3)[NH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:21]([O:24][CH2:25][C:26]1[C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=[CH:28][C:27]=1[N:41]1[CH2:53][CH2:52][N:44]2[C:45]3[CH2:46][CH2:47][CH2:48][CH2:49][C:50]=3[CH:51]=[C:43]2[C:42]1=[O:54])(=[O:23])[CH3:22]>>[C:21]([O:24][CH2:25][C:26]1[C:27]([N:41]2[CH2:53][CH2:52][N:44]3[C:45]4[CH2:46][CH2:47][CH2:48][CH2:49][C:50]=4[CH:51]=[C:43]3[C:42]2=[O:54])=[CH:28][CH:29]=[CH:30][C:31]=1[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[C:14]([CH:16]3[CH2:19][N:18]([CH3:20])[CH2:17]3)[NH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 580438772-(2-(Acetoxymethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-oneHCID 68096887HCID 68096887, compound

Product 1

HCID 58044223HCID 58044223, compoundYield 20%

Procedure

Following Example 136e, 168b and 2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate 114a were reacted to give 168c in 20% yield.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-faa694cffc2243b8987f5c28f9ed74c0
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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