6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one → 4-[2-(Cyclohexylmethoxy)-4-(methylamino)-3-nitrophenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 1057001Notes

Reaction equation

HRID 1057001 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[C:5]2[CH:17]=[CH:18][N:19]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:4]=2[C:3]1=[O:30].Br[C:32]1[CH:39]=[CH:38][C:35]([NH:36][CH3:37])=[C:34]([N+:40]([O-:42])=[O:41])[C:33]=1[O:43][CH2:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1>>[CH:45]1([CH2:44][O:43][C:33]2[C:34]([N+:40]([O-:42])=[O:41])=[C:35]([NH:36][CH3:37])[CH:38]=[CH:39][C:32]=2[C:6]2[C:5]3[CH:17]=[CH:18][N:19]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[C:4]=3[C:3](=[O:30])[N:2]([CH3:1])[CH:7]=2)[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]1

Participants

3

Reactant 2

HCID 867210626-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-oneHCID 1180939244-Bromo-3-(cyclohexylmethoxy)-N-methyl-2-nitroaniline

Product 1

HCID 1180938684-[2-(Cyclohexylmethoxy)-4-(methylamino)-3-nitrophenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Procedure

This compound was synthesized according to the procedure of Example 10, Step 5, using 6-methyl-1-[(4-methylphenyl)sulfonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one and 4-bromo-3-(cyclohexylmethoxy)-N-methyl-2-nitroaniline as the starting materials. LCMS calculated for C29H33N4O6S (M+H)+: m/z=565.2. found: 565.1.

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-1bcbb950b6774aaeb5cfefb83c962eed
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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