Dimethylformamide → HCID 136141615, compound

HRID 1064198Notes

Reaction equation

HRID 1064198 reaction equation
[C:1]([O-:4])([O-])=[O:2].[Na+].[Na+].Br[C:8]1[NH:9][C:10]2[CH:11]=[C:12]([NH:22]C([C@@H]3C[C@H]3C3C=CC=CC=3)=O)[CH:13]=[C:14]3[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:16]=1[C:15]=23.[CH3:34][N:35]([CH3:38])C=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]>[C:14]([O:4][C:1]([N:35]1[CH2:38][CH:10]=[C:11]([C:8]2[NH:9][C:10]3[CH:11]=[C:12]([NH2:22])[CH:13]=[C:14]4[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:16]=2[C:15]=34)[CH2:12][CH2:34]1)=[O:2])([CH3:20])([CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 136141620HCID 136141620, compound

Product 1

HCID 136141615HCID 136141615, compoundYield 82%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
80 °C

Procedure

In a manner analogous to that of Example 184, 2.0 M aqueous Na2CO3 (0.66 mL) was added to a mixture of Intermediate 206(a) of Example 206 (1 g, 3.17 mmol), 4-(4,4,5,5-tetramethyl-[1,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.18 g, 3.82 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.13 g, 0.159 mmol) in anhydrous N,N-dimethylformamide (50 ml), and the reaction was heated at 80° C. for 16 hours. When the reaction was judged complete, the volatile components were removed in vacuo. Ethyl acetate (50 mL), methanol (5 mL) and H2O (500 mL) were added, and the aqueous layer was extracted with ethyl acetate (3×20 mL). The combined ethyl acetate extracts were washed with H2O (2×50 mL) and brine (50 mL) and allowed to dry over Na2SO4. Following filtration, the volatile components were removed in vacuo and CH2Cl2 was added to the residue. The resulting solid was collected by filtration and washed with CH2Cl2 and diethyl ether to afford Intermediate 220(a) (1 g, 2.62 mmol) as a red solid in 82% yield.

Workup

  1. customthe volatile components were removed in vacuo
  2. additionEthyl acetate (50 mL), methanol (5 mL) and H2O (500 mL) were added
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×20 mL)
  4. washThe combined ethyl acetate extracts were washed with H2O (2×50 mL) and brine (50 mL)
  5. dry with materialto dry over Na2SO4
  6. filtrationfiltration
  7. customthe volatile components were removed in vacuo and CH2Cl2
  8. additionwas added to the residue
  9. filtrationThe resulting solid was collected by filtration
  10. washwashed with CH2Cl2 and diethyl ether

Sources & evidence

ORD record
ord-0ff2edc05b8c49b881d67bc1c370a9a3
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

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