[3-(Butylcarbamoyl)phenyl]boronic acid → HCID 67385353, compound

HRID 2096465Notes

Reaction equation

HRID 2096465 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]([NH:29][C:30]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)=[O:31])[CH2:26][CH2:27][CH3:28]>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:36]4[CH:37]=[C:32]([CH:33]=[CH:34][CH:35]=4)[C:30]([NH:29][CH2:25][CH2:26][CH2:27][CH3:28])=[O:31])[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 3693263[3-(Butylcarbamoyl)phenyl]boronic acidHCID 584237682'-amino-6-bromo-1'-methyl-2-phenylspiro[chroman-4,4'-imidazol]-5'(1'H)-one

Product 1

HCID 67385353HCID 67385353, compoundYield 51.4%

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, 0.05 mmol) in 1,4-dioxane (1 mL), Cs2CO3 (2 N, 0.3 mL) and 3-(butylcarbamoyl)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 3-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro-[chroman-4,4′-imidazole]-6-yl)-N-butylbenzamide (12.4 mg, 50%). cis (2.50 mg, 10%). 1H-NMR (MeOD): 0.95 (m, 3H), 1.42 (m, 2H), 1.60 (m, 2H), 2.14 (d, 1H), 2.31 (t, 1H), 3.33 (s, 3H), 3.36 (d, 2H), 5.88 (d, 1H), 7.04 (d, 1H), 7.24 (s, 1H), 7.37 (m, 1H), 7.41 (t, 2H), 7.48 (d, 3H), 7.53 (d, 1H), 7.66 (d, 1H), 7.69 (d, 1H), 7.94 (s, 1H). trans (9.91 mg, 40%). 1H-NMR (MeOD): 0.96 (t, 3H), 1.43 (m, 2H), 1.61 (m, 2H), 2.03 (d, 1H), 2.52 (t, 1H), 3.33 (s, 3H), 3.39 (d, 2H), 5.30 (d, 1H), 7.05 (d, 1H), 7.25 (s, 1H), 7.39 (m, 1H), 7.42 (t, 2H), 7.47 (d, 3H), 7.53 (d, 1H), 7.67 (d, 1H), 7.70 (d, 1H), 7.93 (s, 1H).

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-c44b2d9170464b20b58fa35d0b091e98
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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