Sodium Carbonate → HCID 67247802, compound

HRID 2175089Notes

Reaction equation

HRID 2175089 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]([O:11][C:12](=[O:32])[NH:13][CH:14]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]3[N:30]=[C:29](Cl)[N:28]=[CH:27][N:26]=3)[CH2:21][CH2:20]2)[CH2:15]1)([CH3:10])([CH3:9])[CH3:8].CC1(C)C(C)(C)OB([C:41]2[CH:50]=[CH:49][C:48]3[C:47]([CH3:52])([CH3:51])[CH2:46][CH2:45][C:44]([CH3:54])([CH3:53])[C:43]=3[CH:42]=2)O1>CN(C=O)C.COCCOC.CO.O.CO.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>[C:7]([O:11][C:12](=[O:32])[NH:13][CH:14]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]3[N:30]=[C:29]([C:50]4[CH:41]=[CH:42][C:43]5[C:44]([CH3:54])([CH3:53])[CH2:45][CH2:46][C:47]([CH3:52])([CH3:51])[C:48]=5[CH:49]=4)[N:28]=[CH:27][N:26]=3)[CH2:21][CH2:20]2)[CH2:15]1)([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolaneHCID 53252487HCID 53252487, compound

Product 1

HCID 67247802HCID 67247802, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 86609212HCID 86609212, compoundSolvent

Procedure

23 mg (0.22 mmol) of sodium carbonate are added to 50 mg (0.11 mmol) of {1-[1-(4-chloro-1,3,5-triazin-2-yl)piperidin-4-yl]pyrrolidin-3-yl}carbamic acid tert-butyl ester and 45 mg (0.12 mmol) of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane in 1.5 ml of DMF/DME/methanol/water (1/1/0.9/0.3). The reaction mixture is degassed a number of times, 8 mg (0.017 mmol) of bis(triphenylphosphine)palladium(II) dichloride are added under nitrogen atmosphere, the mixture is treated in an ultrasound bath for 10 min and subsequently irradiated in the microwave at 100° C. for 20 min. The reaction mixture is diluted with methanol, filtered, and the crude product is purified by means of preparative HPLC.

Workup

  1. additionare added under nitrogen atmosphere
  2. additionthe mixture is treated in an ultrasound bath for 10 min
  3. customsubsequently irradiated in the microwave at 100° C. for 20 min
  4. filtrationfiltered
  5. customthe crude product is purified by means of preparative HPLC

Sources & evidence

ORD record
ord-bc40e84e77fe4dbeb5cf18723a2cb09f
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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