1,2-Dimethoxyethane → HCID 178502315, compound

HRID 1751427Notes

Reaction equation

HRID 1751427 reaction equation
CC(C)[C@H:3]([NH:33][C:34](=[O:37])[O:35][CH3:36])[C:4](=[O:32])[N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:14][C:13]2[C:15]3[C:20]([CH:21]=[CH:22][C:12]=2[N:11]=1)=[CH:19][C:18](B1OC(C)(C)C(C)(C)O1)=[CH:17][CH:16]=3.Br[C:40]1[CH:41]=[C:42]2[C:47](=[CH:48][CH:49]=1)[CH:46]=[C:45]([C:50]1[NH:54][C:53]([C@@H:55]3[CH2:59][CH2:58][CH2:57][N:56]3[C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])=[N:52][CH:51]=1)[CH:44]=[CH:43]2.[C:67]([O-])([O-])=O.[K+].[K+].CO[CH2:75][CH2:76]OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:36][O:35][C:34]([NH:33][C@@H:3]([CH:75]([CH3:76])[CH3:67])[C:4]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:14][C:13]2[C:15]3[C:20]([CH:21]=[CH:22][C:12]=2[N:11]=1)=[CH:19][C:18]([C:40]1[CH:41]=[C:42]2[C:47](=[CH:48][CH:49]=1)[CH:46]=[C:45]([C:50]1[NH:54][C:53]([C@@H:55]4[CH2:59][CH2:58][CH2:57][N:56]4[C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])=[N:52][CH:51]=1)[CH:44]=[CH:43]2)=[CH:17][CH:16]=3)=[O:32])=[O:37]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 59610569HCID 59610569, compoundHCID 178502307HCID 178502307, compound

Product 1

HCID 178502315HCID 178502315, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Methyl (S)-3-methyl-1-oxo-1-((S)-2-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (267 mg, 0.513 mmol), (S)-tert-butyl 2-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (272 mg, 0.616 mmol), Pd(PPh3)4 (59 mg, 0.0513 mmol) and K2CO3 (2M in H2O, 0.62 mL, 1.2 mmol) were suspended in DME (5 mL). The mixture was degassed with N2 for 10 min then heated to reflux. After 5 h, the reaction mixture was cooled to RT, diluted with EtOAc and washed with brine. The organic phase was dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (0% to 30% MeOH/EtOAc) to afford the title compound (201 mg, 52%).

Workup

  1. customThe mixture was degassed with N2 for 10 min
  2. temperaturethen heated to reflux
  3. additiondiluted with EtOAc
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by silica column chromatography (0% to 30% MeOH/EtOAc)

Sources & evidence

ORD record
ord-9bb64dbe33bf407a91665798a9448411
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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