Toluene → HCID 66661862, compound

HRID 2275559Notes

Reaction equation

HRID 2275559 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH2:16][C:15]4([C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[C:19](=[O:26])[O:18]4)[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[N:28]1.C1(C)C=CC=CC=1.CN[C@H]1CCCC[C@@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I>[N:27]1[N:28]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:11]([N:13]4[CH2:17][CH2:16][C@@:15]5([C:25]6[CH:24]=[CH:23][N:22]=[CH:21][C:20]=6[C:19](=[O:26])[O:18]5)[CH2:14]4)=[O:12])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:29]=[C:30]2[C:35]=1[CH:34]=[CH:33][CH:32]=[CH:31]2

Participants

7

Reactant 5

HCID 1140TolueneHCID 92211H-IndazoleHCID 62657Potassium Phosphate, TribasicHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 66661505HCID 66661505, compound

Product 1

HCID 66661862HCID 66661862, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

To a solution of 1′-{[1-(4-bromophenyl)cyclopropyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one (30 mg, 0.00007 mol), 1H-Indazole (10.3 mg, 0.0000871 mol) in toluene (1 mL, 0.01 mol) were added (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (2.1 mg, 0.000014 mol), copper(I) iodide (1 mg, 0.000007 mol), and potassium phosphate (32.4 mg, 0.000152 mol) in a sealed vial. The mixture was microwaved at 150 Celsius for 60 minutes. Then the mixture was cooled down to r.t. and filtered. The filtrate was diluted with methanol, and the desired compound was obtained by revised phase prep-HPLC. MS (ESI): 451.1 (M+H+). The enantiomers were separated by chiral HPLC.

Workup

  1. customThe mixture was microwaved at 150 Celsius for 60 minutes
  2. filtrationfiltered
  3. additionThe filtrate was diluted with methanol

Sources & evidence

ORD record
ord-dec02bec56b64eacaa5172bf89ec1f28
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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