Cesium carbonate → HCID 71469142, compound

HRID 2368183Notes

Reaction equation

HRID 2368183 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])[CH:11]=[CH:12][CH:13]=2)[C:5]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][N:3]=1.[O:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:26]1[CH2:27][CH2:28][N:29]([C:32]2[CH:33]=[CH:34][C:35]([NH:36][C:2]3[N:7]=[C:6]([C:8]4[CH:9]=[C:10]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])[CH:11]=[CH:12][CH:13]=4)[C:5]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:4][N:3]=3)=[CH:37][CH:38]=2)[CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 71469141HCID 71469141, compound

Product 1

HCID 71469142HCID 71469142, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
200 °C

Procedure

N-(3-(2-Chloro-5-(phenylamino)pyrimidin-4-yl)phenyl)acrylamide (30 mg, 0.086 mmol), 4-morpholinoaniline (15.24 mg, 0.086 mmol) and Cs2CO3 (33.4 mg, 0.103 mmol) were dissolved in toluene (4.5 mL) in a sealable microwave compatible reaction tube, then tris(dibenzylideneacetone)-dipalladium(0) (Pd2(dba)3; 1.566 mg, 1.710 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (1.979 mg, 3.42 μmol) were added. The reaction tube was sealed and the reaction was heated under microwave irradiation (30 min, 200° C., 3 atm). After completion of the reaction, solvent was removed by vacuum and product was purified by flash column chromatography. 1H NMR (400 MHz, CD3OD): δ 8.32 (s, 1H), 8.21 (s, 1H), 7.69-7.61 (m, 4H), 7.30 (t, 1H, J=8.0 Hz), 7.07 (m, 2H), 6.95 (m, 2H), 6.65 (m, 3H), 6.42-6.37 (m, 2H), 5.76 (dd, 1H, J=2.4 and 9.6 Hz), 3.82 (m, 4H), 3.08 (m, 4H); ESI-MS: [M+H]+.

Workup

  1. customThe reaction tube was sealed
  2. customAfter completion of the reaction, solvent
  3. customwas removed by vacuum and product
  4. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-d394102efcc648998648c737eec4fa95
Source dataset
uspto-grants-2014_04
Patent number
US08703767B2

Reaction notes

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