Cesium carbonate → HCID 117652439, compound

HRID 1500821Notes

Reaction equation

HRID 1500821 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]3[NH:12][C:13]4[C:18]([CH:19]=3)=[CH:17][CH:16]=[C:15]([CH3:20])[CH:14]=4)=[CH:9][N:8]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:5]2=[N:6][CH:7]=1.[C:40]([NH:44][C:45]1[CH:46]=[C:47](B(O)O)[CH:48]=[CH:49][CH:50]=1)(=[O:43])[CH:41]=[CH2:42].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:20][C:15]1[CH:14]=[C:13]2[C:18]([CH:19]=[C:11]([C:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([C:47]5[CH:46]=[C:45]([NH:44][C:40](=[O:43])[CH:41]=[CH2:42])[CH:50]=[CH:49][CH:48]=5)[N:3]=4)[N:8]([C:21]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:9]=3)[NH:12]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 103213313-Acrylamidophenylboronic acidHCID 117652485HCID 117652485, compound

Product 1

HCID 117652439HCID 117652439, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-bromo-7-(6-methyl-1H-indol-2-yl)-5-trityl-5H-pyrrolo[2,3-b]pyrazine 8 (30 mg, 0.0528 mmol) and (3-acrylamidophenyl)boronic acid 2 (10.9 mg, 0.0528 mmol) in DMF was added cesium carbonate (34.74 mg, 0.1056 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(PPh3)Cl2 (2.06 mg, 0.00264 mmol) was added to the reaction and again degassed for 15 min. The reaction was stirred for 2 h at 90° C. The reaction mixture was allowed to cool to rt. The reaction was diluted with DCM filtered through Celite. The organic layer was concentrated to get the crude. The resulting oil was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 40% ethyl acetate in hexane to afford off white colour solid compound N-(3-(7-(6-methyl-1H-indol-2-yl)-5-trityl-5H-pyrrolo[2,3-b]pyrazin-2-yl)phenyl)acrylamide 9.

Workup

  1. customThe reaction was degassed
  2. custompurged with nitrogen for 10 min
  3. customagain degassed for 15 min
  4. temperatureto cool to rt
  5. additionThe reaction was diluted with DCM
  6. filtrationfiltered through Celite
  7. concentrationThe organic layer was concentrated
  8. customto get the crude
  9. customThe resulting oil was purified through flash chromatography
  10. washThe compound was eluted at 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-95d6bf89ce574f9ea8cc97f5a61edb04
Source dataset
uspto-grants-2015_12
Patent number
US09206188B2

Reaction notes

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