6-(3-cyclopropyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)indolin-2-one → (R)-4-((R)-1-((3-cyclopropyl-6-(3,3-dimethylindolin-6-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one

HRID 2209102Notes

Reaction equation

HRID 2209102 reaction equation
[CH:1]1([N:4]2[C:8]3[C:9]([O:23][C@@H:24]([C@@H:26]4[CH2:30][C:29](=[O:31])[NH:28][CH2:27]4)[CH3:25])=[N:10][C:11](C4C=C5C(CC(=O)N5)=CC=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:3][CH2:2]1.[CH3:32][C:33]1([CH3:51])[C:41]2[C:36](=[CH:37][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:39][CH:40]=2)[NH:35][CH2:34]1>>[CH:1]1([N:4]2[C:8]3[C:9]([O:23][C@@H:24]([C@H:26]4[CH2:27][NH:28][C:29](=[O:31])[CH2:30]4)[CH3:25])=[N:10][C:11]([C:38]4[CH:37]=[C:36]5[C:41]([C:33]([CH3:32])([CH3:51])[CH2:34][NH:35]5)=[CH:40][CH:39]=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 1178438396-(3-cyclopropyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)indolin-2-oneHCID 1238475863,3-Dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline

Product 1

HCID 117842893(R)-4-((R)-1-((3-cyclopropyl-6-(3,3-dimethylindolin-6-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-oneYield 19%

Procedure

Prepared by Suzuki coupling reaction procedure, as previously described for the synthesis of 6-(3-cyclopropyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)indolin-2-one:, using instead 3,3-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline as a starting material to afford 22.0 mg (19%) of (R)-4-((R)-1-((3-cyclopropyl-6-(3,3-dimethylindolin-6-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one:. 1H NMR (300 MHz, d6-DMSO) δ 8.24 (s, 1H), 7.56 (s, 2H), 7.25 (dd, J=7.7 Hz, J=1.4 Hz, 1H), 7.15 (d, J=1.5 Hz, 1H), 7.01 (d, J=7.7 Hz, 1H), 5.53 (m, 2H), 3.68 (m, 1H), 3.41 (m, 1H), 3.20 (m, 3H), 2.82 (m, 1H), 2.33 (m, 2H), 1.40 (d, J=6.2 Hz, 3H), 1.23 (s, 6H), 1.18 (m, 5H). MS (ESI+) m/z 432.2 (M+H).

Workup

  1. customPrepared by Suzuki
  2. customreaction procedure

Sources & evidence

ORD record
ord-1b45ca5335fe4de4b4b48e9283ae2c7d
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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