Potassium Carbonate → HCID 178502313, compound

HRID 1751353Notes

Reaction equation

HRID 1751353 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:28](=[CH:29][CH:30]=1)[C:8]1[NH:9][C:10]([C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17](=[O:27])[C@@H:18]([NH:22][C:23](=[O:26])[O:24][CH3:25])[CH:19]([CH3:21])[CH3:20])=[N:11][C:7]=1[CH:6]=[CH:5]2.CC1(C)C(C)(C)OB([C:39]2[CH:40]=[C:41]3[C:63](=[CH:64][CH:65]=2)[C:45]2[NH:46][C:47]([C@@H:49]4[C@@H:54]5[CH2:55][C@@H:51]([CH2:52][CH2:53]5)[N:50]4[C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])=[N:48][C:44]=2[CH2:43][CH2:42]3)O1.C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[C:59]([O:58][C:56]([N:50]1[C@H:49]([C:47]2[NH:46][C:45]3[C:63]4[C:41]([CH2:42][CH2:43][C:44]=3[N:48]=2)=[CH:40][C:39]([C:2]2[CH:3]=[C:4]3[C:28](=[CH:29][CH:30]=2)[C:8]2[NH:9][C:10]([C@@H:12]5[CH2:16][CH2:15][CH2:14][N:13]5[C:17](=[O:27])[C@@H:18]([NH:22][C:23]([O:24][CH3:25])=[O:26])[CH:19]([CH3:21])[CH3:20])=[N:11][C:7]=2[CH:6]=[CH:5]3)=[CH:65][CH:64]=4)[C@@H:54]2[CH2:55][C@H:51]1[CH2:52][CH2:53]2)=[O:57])([CH3:62])([CH3:60])[CH3:61]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 178452511HCID 178452511, compoundHCID 178502308HCID 178502308, compound

Product 1

HCID 178502313HCID 178502313, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Methyl (S)-1-((S)-2-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (482 mg, 1.02 mmol) and (1R,3S,4S)-tert-butyl 3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,5-dihydro-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (552 mg, 1.12 mmol) were combined in DME (12 mL). Pd(PPh3)4 (118 mg, 0.102 mmol) and K2CO3 (2M H2O, 1.68 mL, 3.36 mmol) were added, and the solution was degassed with N2 for 10 min. The solution was heated to 85° C. and stirred o/n. The following morning, the solution was cooled to rt. The solution was diluted with EtOAc, washed with sat. NaHCO3, brine, dried with MgSO4, and concentrated. The residue was purified by silica gel chromatography to yield product (307 mg).

Workup

  1. customthe solution was degassed with N2 for 10 min
  2. temperatureThe following morning, the solution was cooled to rt
  3. additionThe solution was diluted with EtOAc
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-91986f30dd6e4d0c907f68c71ffbc25d
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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