Ethyl Acetate → HCID 57660952, compound

HRID 1424319Notes

Reaction equation

HRID 1424319 reaction equation
CC1C=CN=C(NCC2CCN(C3C=CC(CC([NH:27][C:28](=[O:38])[C:29]4[C:34]([CH3:35])=[CH:33][C:32]([CH3:36])=[CH:31][C:30]=4[CH3:37])C(O)=O)=CC=3)CC2)C=1.[C:39]([O:43][C:44](=[O:60])[N:45]([C:53]1[CH:58]=[C:57]([CH3:59])[CH:56]=[CH:55][N:54]=1)[CH2:46][CH:47]1[CH2:52][CH2:51][NH:50][CH2:49]C1)([CH3:42])([CH3:41])[CH3:40].[C:61]([O-])([O-])=[O:62].[Cs+].[Cs+].C[C:68]1(C)[C:94]2[C:89](=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:88][C:70]2[C:71](P(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:72][CH:73]=[CH:74][C:69]1=2.C(OCC)(=[O:111])C>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].C(Cl)(Cl)Cl>[CH3:61][O:62][C:89](=[O:88])[CH:94]([NH:27][C:28](=[O:38])[C:29]1[C:30]([CH3:37])=[CH:31][C:32]([CH3:36])=[CH:33][C:34]=1[CH3:35])[CH2:68][C:69]1[CH:70]=[CH:71][C:72]([N:50]2[CH2:49][CH:47]([CH2:46][N:45]([C:44]([O:43][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:60])[C:53]3[CH:58]=[C:57]([CH3:59])[CH:56]=[CH:55][N:54]=3)[CH2:52][C:51]2=[O:111])=[CH:73][CH:74]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 16678135HCID 16678135, compoundHCID 57660929HCID 57660929, compound

Product 1

HCID 57660952HCID 57660952, compound

Reagents, catalysts & solvents 1

HCID 11072516HCID 11072516, compoundCatalyst

Procedure

45 mg (0.074 mmol) of (8), 50 mg (0.123 mmol) of (7), 48 mg (0.148 mmol) of Cs2CO3, 16 mg (0.024 mmol) of Pd(dba)2-CHCl3 and 43 mg (0.074 mmol) of Xantphos were heated under argon for 3 hours. After diluting with 50 ml ethyl acetate and washing two times with saturated aqueous NaHCO3 and one time with brine the solution was dried over Na2SO4 and concentrated in vacuo. 70 mg of crude (15) were obtained as yellow foam.

Workup

  1. washwashing two times with saturated aqueous NaHCO3 and one time with brine the solution
  2. dry with materialwas dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b4cad4e707e4324bc55a94e97f19380
Source dataset
uspto-grants-2015_01
Patent number
US08927534B2

Reaction notes

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