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-(4-Amino-2-(cyclopropylmethoxy)-3-nitrophenyl)-6-methyl-l-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

HRID 1056948Notes

Reaction equation

HRID 1056948 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][CH2:13][CH:14]1[CH2:16][CH2:15]1.[CH3:17][N:18]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[C:21]2[CH:33]=[CH:34][N:35]([S:36]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[C:20]=2[C:19]1=[O:46]>>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([C:22]2[C:21]3[CH:33]=[CH:34][N:35]([S:36]([C:39]4[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=4)(=[O:38])=[O:37])[C:20]=3[C:19](=[O:46])[N:18]([CH3:17])[CH:23]=2)=[C:3]([O:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)[C:4]=1[N+:9]([O-:11])=[O:10]

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 118093886HCID 118093886, compound

Product 1

HCID 1180939284-(4-Amino-2-(cyclopropylmethoxy)-3-nitrophenyl)-6-methyl-l-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

Procedure

This compound was synthesized according to the procedure of Example 10, Step 5, using 4-bromo-3-(cyclopropylmethoxy)-2-nitroaniline and 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 as the starting materials. LCMS calculated for C25H25N4O6S (M+H)+: m/z=509.1. found: 509.1.

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-eaee44b3bc8445e3b70ec8d7bc2f440d
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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