4-(Diethylcarbamoyl)phenylboronic Acid → 4-(2'-amino-1'-methyl-5'-oxo-2-phenyl-1',5'-dihydro-spiro[chroman-4,4'-imidazole]-6-yl)-N,N-diethylbenzamide

HRID 2096492Notes

Reaction equation

HRID 2096492 reaction equation
[NH2:1][C:2]1[N:3]([CH3:24])[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1.[CH2:25]([N:27]([CH2:39][CH3:40])[C:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:29])[CH3:26]>O1CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:3]([CH3:24])[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:33]4[CH:34]=[CH:35][C:30]([C:28]([N:27]([CH2:25][CH3:26])[CH2:39][CH3:40])=[O:29])=[CH:31][CH:32]=4)[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1

Participants

6

Reactant 2

HCID 27733754-(Diethylcarbamoyl)phenylboronic AcidHCID 584237682'-amino-6-bromo-1'-methyl-2-phenylspiro[chroman-4,4'-imidazol]-5'(1'H)-one

Product 1

HCID 584242434-(2'-amino-1'-methyl-5'-oxo-2-phenyl-1',5'-dihydro-spiro[chroman-4,4'-imidazole]-6-yl)-N,N-diethylbenzamideYield 28%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 10796Cesium carbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Pd(PPh3)2Cl2 (10 mg) in a 10 mL CEM test tube under Ar was treated sequentially with 2′-amino-6-bromo-1′-methyl-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 0.052 mmol) in 1,4-dioxane (1 mL), Cs2CO3 (2 N, 0.3 mL) and 4-(diethylcarbamoyl)phenylboronic acid (23 mg, 0.1 mmol). The mixture was heated in a microwave reactor at 120° C. for 30 mins. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to give pure 4-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydro-spiro[chroman-4,4′-imidazole]-6-yl)-N,N-diethylbenzamide (6.95 mg, 28%). 1H-NMR (MeOD): 1.13 (s, 3H), 1.24 (d, 3H), 2.13 (d, 1H), 2.30 (s, 1H), 3.17 (s, 3H), 3.32 (d, 4H), 5.91 (d, 1H), 7.03 (d, 1H), 7.22 (s, 1H), 7.33 (m, 1H), 7.40 (m, 4H), 7.49 (m, 2H), 7.51 (m, 1H), 7.57 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give the residue, which
  3. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-37f6a60155cf4569a48f233f8592a7d8
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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