Sodium Carbonate → N,N-dimethyl-4-(7-(1-oxoisoindolin-2-yl)-5-trityl-5H-pyrrolo[2,3-b]pyrazin-2-yl)benzamide

HRID 627790Notes

Reaction equation

HRID 627790 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([N:11]3[CH2:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:20])=[CH:9][N:8]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:5]2=[N:6][CH:7]=1.[CH3:40][N:41]([CH3:53])[C:42]([C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1)=[O:43].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH3:40][N:41]([CH3:53])[C:42](=[O:43])[C:44]1[CH:45]=[CH:46][C:47]([C:2]2[N:3]=[C:4]3[C:10]([N:11]4[CH2:19][C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[C:12]4=[O:20])=[CH:9][N:8]([C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:5]3=[N:6][CH:7]=2)=[CH:48][CH:49]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 35037674-(Dimethylcarbamoyl)phenylboronic AcidHCID 866765062-(2-Bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl)isoindolin-1-one

Product 1

HCID 71143648N,N-dimethyl-4-(7-(1-oxoisoindolin-2-yl)-5-trityl-5H-pyrrolo[2,3-b]pyrazin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

2-(2-bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl)isoindolin-1-one (20 mg, 0.3500 mmol), [4-(dimethylcarbamoyl)phenyl]boronic acid (81.06 mg, 0.4200 mmol) and Na2CO3 (525.0 μL of a 2M aqueous solution, 1.050 mmol) combined in 1,4-dioxane (3 mL) and the mixture de-gassed (×2 vacuum-N2 cycles). Pd(tBu3P)2 (17.89 mg, 0.03500 mmol) added and the mixture de-gassed (×2 cycles) then heated at 65° C. overnight. Reaction mixture cooled to ambient and partitioned between DCM and water. Aqueous phase extracted with DCM and combined organics dried and concentrated to a yellow solid, which is taken up in DCM (4 mL) under N2 and used in the next step without further purification.

Workup

  1. customthe mixture de-gassed (×2 vacuum-N2 cycles)
  2. customthe mixture de-gassed (×2 cycles)
  3. customReaction mixture
  4. temperaturecooled
  5. custompartitioned between DCM and water
  6. extractionAqueous phase extracted with DCM
  7. customcombined organics dried
  8. concentrationconcentrated to a yellow solid, which
  9. customused in the next step without further purification

Sources & evidence

ORD record
ord-a48c823563584a69b1e115036416df5a
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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