Sodium Carbonate → HCID 66905104, compound

HRID 1692080Notes

Reaction equation

HRID 1692080 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:10]1=[O:20].[C:30]([O:34][C:35]([C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1)=[O:36])([CH3:33])([CH3:32])[CH3:31].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C(OCC)(=O)C.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:30]([O:34][C:35]([C:37]1[CH:42]=[CH:41][C:40]([C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([CH2:8][C@@H:9]3[CH2:13][CH2:12][N:11]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[C:10]3=[O:20])=[C:6]([Cl:21])[CH:5]=2)=[CH:39][CH:38]=1)=[O:36])([CH3:33])([CH3:31])[CH3:32]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2773301(4-((Tert-butoxy)carbonyl)phenyl)boronic acidHCID 86630015HCID 86630015, compound

Product 1

HCID 66905104HCID 66905104, compoundYield 74.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bring a mixture of (R)-trifluoro-methanesulfonic acid 3,5-dichloro-4-(1-morpholin-4-yl-2-oxo-pyrrolidin-3-ylmethyl)-phenyl ester (0.19 g, 0.4 mmol), 4-t-butyloxycarbonylphenylboronic acid (0.106 g, 0.48 mmol), sodium carbonate (0.127 g, 1.2 mmol) in THF (10 mL) and water (3 mL) to 60° C. To the mixture at 60° C., add Pd(PPh3)4 (0.023 g, 0.02 mmol) and then raise reaction temperature to 80° C. and stir for 3 hours. Cool the reaction, dilute with ethyl acetate, and wash with water and brine. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and then purify on silica gel column with 40% ethyl acetate in hexanes to afford 0.15 g (74%) of the titled product. MS (m/z): 461 (M+).

Workup

  1. temperatureraise
  2. customreaction temperature to 80° C.
  3. temperatureCool
  4. customthe reaction
  5. washwash with water and brine
  6. dry with materialDry the organic layer (Na2SO4)
  7. customremove the solvent in vacuo
  8. customto afford crude product
  9. custompurify on silica gel column with 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-50eff8a4791a43dfa989a3708d7975c4
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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