Bicarbonate Ion → HCID 11617867, compound

HRID 2235264Notes

Reaction equation

HRID 2235264 reaction equation
Br[C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16].C([O-])([O-])=O.[Cs+].[Cs+].C(=O)(O)[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]>[CH2:4]([C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16])[C:3]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:2]=1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 10796Cesium carbonateHCID 11632109HCID 11632109, compound

Product 1

HCID 11617867HCID 11617867, compoundYield 121.1%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Charge a flask with 3-(2-bromo-6-chloro-benzyl)-1-cyclohexyl-pyrrolidin-2-one (Example 56) (250 mg, 0.67 mmol), Pd(dppf)Cl2 (54 mg, 0.067 mmol) and Cs2CO3 (660 mg, 2.0 mmol) and purge with nitrogen. Add DMF (6 mL) and water (0.6 mL) and stir. Add Bn-9-BBN (0.5 M, 4.0 mL, 2.0 mmol) and heat to 60° C. for 1 hour. Pour into saturated aqueous bicarbonate and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Purify over silica gel (10% ethyl acetate in hexanes) to yield 155 mg (60%) of the title compound as a clear colorless oil. Mass spectrum (apci) m/z=382.3 (M+H).

Workup

  1. custompurge with nitrogen
  2. extractionextract with methylene chloride
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify over silica gel (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c8b3f0e00bfb4b2d9943539213be002b
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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