Potassium Carbonate → HCID 69675359, compound

HRID 1751349Notes

Reaction equation

HRID 1751349 reaction equation
[CH3:1][CH:2]([CH3:46])[C@H:3]([NH:41][C:42](=[O:45])[O:43][CH3:44])[C:4](=[O:40])[N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]([C:15]2[CH:28]=[C:27]3[C:29]4[C:30]5[C:24]([CH2:25][CH2:26]3)=[CH:23][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:21][C:20]=5[CH2:19][CH2:18][C:17]=4[CH:16]=2)=[CH:13][N:14]=1.Br[C:48]1[NH:52][C:51]([C@@H:53]2[CH2:57][CH2:56][CH2:55][N:54]2[C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])=[N:50][CH:49]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CS(C)=O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].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>[CH3:44][O:43][C:42]([NH:41][C@@H:3]([CH:2]([CH3:46])[CH3:1])[C:4]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]([C:15]2[CH:16]=[C:17]3[C:29]4[C:30]5[C:20](=[CH:21][C:22]([C:48]6[NH:52][C:51]([C@@H:53]7[CH2:57][CH2:56][CH2:55][N:54]7[C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])=[N:50][CH:49]=6)=[CH:23][C:24]=5[CH2:25][CH2:26][C:27]=4[CH:28]=2)[CH2:19][CH2:18]3)=[CH:13][N:14]=1)=[O:40])=[O:45]

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 56605192tert-Butyl (2S)-2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylateHCID 67681755HCID 67681755, compound

Product 1

HCID 69675359HCID 69675359, compoundYield 33.8%

Reagents, catalysts & solvents 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5,9,10-tetrahydropyren-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (139 mg, 0.22 mmol) and (S)-tert-butyl 2-(5-bromo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (77 mg, 0.24 mmol) were dissolved in dioxane (2 mL) and DMSO (2 mL). Pd(dppf)2Cl2 (16 mg, 0.022 mmol), Pd(PPh3)4 (25 mg, 0.022 mmol), and K2CO3 (2M in H2O, 0.33 mL, 0.66 mmol). The tube was sealed and heated to 100° C. for 20 h. The mixture was cooled to rt, diluted with EtOAc, and washed with sat. NaHCO3, brine, dried with MgSO4, and concentrated. The residue was purified by silica gel chromatography to yield product (54.5 mg).

Workup

  1. customThe tube was sealed
  2. temperatureThe mixture was cooled to rt
  3. washwashed with sat. NaHCO3, brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-684d96f09f63465dbf827cea9ea93dac
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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