Sodium Carbonate → HCID 10435982, compound

HRID 1180420Notes

Reaction equation

HRID 1180420 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:14]([CH2:16][NH:17][C:18](=[O:47])[C@@H:19]([O:24][CH:25]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][CH:27]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])#[N:15].[N].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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]([CH2:16][NH:17][C:18](=[O:47])[C@@H:19]([O:24][C@@H:25]([C:41]1[CH:42]=[CH:43][C:44]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=2)=[CH:45][CH:46]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])#[N:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 116228514-(4-Bromophenyl)morpholineHCID 178446061HCID 178446061, compound

Product 1

HCID 10435982HCID 10435982, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of N-(4-bromophenyl)morpholine (0.66 mmol, 159 mg) in DMF (7 mL) was added under a stream of nitrogen (2S)-N-(cyanomethyl)-4-methyl-2-{phenyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy}pentanamide from Example 16 (0.66 mmol, 250 mg). PdCl2(dppf) (0.033 mmol, 24 mg) and 2N Na2CO3 (2.63 mmol) was added. The mixture was degassed with a rapid stream of nitrogen bubbling through the mixture and the mixture was heated to 85° C. for 18 h. EtOAc was added, the mixture was washed with water and brine. The organic extract was dried and chromatographed (20-40% EtOAc/hexane) to give the title compound.

Workup

  1. customThe mixture was degassed with a rapid stream of nitrogen bubbling through the mixture
  2. additionEtOAc was added
  3. washthe mixture was washed with water and brine
  4. extractionThe organic extract
  5. customwas dried
  6. customchromatographed (20-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-c77f2e71866f424997f27147b945b5e3
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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