3,3-Dimethyl-1,3-dihydro-indol-2-one → HCID 117842889, compound

HRID 2209264Notes

Reaction equation

HRID 2209264 reaction equation
Cl[C:2]1[CH:3]=[C:4]([O:14][C@@H:15]([C@H:17]2[CH2:21][NH:20][C:19](=[O:22])[CH2:18]2)[CH3:16])[C:5]2[N:6]([N:8]=[CH:9][C:10]=2[CH:11]2[CH2:13][CH2:12]2)[CH:7]=1.[CH3:23][C:24]1([CH3:43])[C:32]2[C:27](=[CH:28][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:31]=2)[NH:26][C:25]1=[O:42].CC1(C)C2C(=CC=CC=2)NC1=O>>[CH:11]1([C:10]2[CH:9]=[N:8][N:6]3[CH:7]=[C:2]([C:29]4[CH:28]=[C:27]5[C:32]([C:24]([CH3:43])([CH3:23])[C:25](=[O:42])[NH:26]5)=[CH:31][CH:30]=4)[CH:3]=[C:4]([O:14][C@@H:15]([C@@H:17]4[CH2:18][C:19](=[O:22])[NH:20][CH2:21]4)[CH3:16])[C:5]=23)[CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-oneHCID 669534833,3-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-oneHCID 131735985HCID 131735985, compound

Product 1

HCID 117842889HCID 117842889, compound

Procedure

Following Steps 7 and 8 from the procedure used to prepare Example 6.53, starting from (R)-4-((R)-1-((6-chloro-3-cyclopropylpyrazolo[1,5-a]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one 6.53a (55 mg) and 3,3-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one, 13 mg of 6-(3-cyclopropyl-4-4R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyridin-6-yl)-3,3-dimethylindolin-2-one was synthesized.

Workup

  1. customto prepare Example 6.53
  2. customwas synthesized

Sources & evidence

ORD record
ord-971f21ade6b24199a170cfce3c55a7f4
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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