Cesium carbonate → HCID 57442339, compound

HRID 2262716Notes

Reaction equation

HRID 2262716 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[O:16])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32].C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:23]1([N:20]2[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][N:11]3[CH2:12][CH2:13][N:8]([C:4]4[CH:5]=[CH:6][C:7]([N:27]5[CH2:31][CH2:30][CH2:29][C:28]5=[O:32])=[CH:2][CH:3]=4)[CH2:9][CH2:10]3)[CH2:18][CH2:19]2)[CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57442338HCID 57442338, compound

Product 1

HCID 57442339HCID 57442339, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

In a sealed tube, place 1-(3-bromophenyl)-4-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]piperazine (150 mg, 0.355 mmol), 2-pyrrolidone (90 mg, 1.07 mmol), Cs2CO3 (346 mg, 1.065 mmol), xantphos (20 mg, 0.036 mmol), and Pd2dba3 (32 mg, 0.355 mmol). Add dioxane (6 mL) and degas the mixture with N2. Seal the tube and heat at 120° C. overnight. Cool and partition between EtOAc (50 mL) and 1N NaOH (50 mL). Extract with EtOAc (2×50 mL). Combine, dry and evaporate the organic extracts. Purify the crude product by PTLC eluting with EtOAc/MeOH/TEA(95:5:5) to yield the title compound. 1H NMR (CDCl3) δ 7.48 (d, 2H) 6.3 (d, 2H), 3.84 (t, 2H), 3.66 (br m, 4H), 3.25 (s, 2H), 3.18 (t, 4H), 2.76-2.57 (m, 7H), 2.35-2.30 (m, 4H), 2.20-2.02 (m, 4H), 1.98-1.86 (m, 2H), 1.77-1.68 (m, 2H); LC-MS (M+1) 426.09.

Workup

  1. customAdd dioxane (6 mL) and degas the mixture with N2
  2. customSeal the tube
  3. temperatureCool
  4. custompartition between EtOAc (50 mL) and 1N NaOH (50 mL)
  5. extractionExtract with EtOAc (2×50 mL)
  6. customCombine, dry
  7. customevaporate the organic extracts
  8. customPurify the crude product by PTLC
  9. washeluting with EtOAc/MeOH/TEA(95:5:5)

Sources & evidence

ORD record
ord-ce5e73c2731e435f978ebd788326470f
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

Loading…