Ammonium Chloride → HCID 59857454, compound

HRID 555421Notes

Reaction equation

HRID 555421 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[O:7][C:8]1[C:13](I)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:19]([Si:22]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[N:23]1[C:31]2[C:26](=[CH:27][C:28]([NH2:32])=[CH:29][N:30]=2)[CH:25]=[CH:24]1)([CH3:21])[CH3:20].CC(C)([O-])C.[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.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.[Fe+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]>[C:1]([C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[O:7][C:8]1[C:13]([NH:32][C:28]2[CH:27]=[C:26]3[CH:25]=[CH:24][N:23]([Si:22]([CH:33]([CH3:35])[CH3:34])([CH:36]([CH3:38])[CH3:37])[CH:19]([CH3:20])[CH3:21])[C:31]3=[N:30][CH:29]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 222736141-[Tri(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridin-5-amineHCID 23676156Sodium t-butoxideHCID 598574352-(2-tert-Butylphenoxy)-3-iodopyridine

Product 1

HCID 59857454HCID 59857454, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-(2-tert-butylphenoxy)-3-iodopyridine (prepared as above) (177 mg, 0.50 mmol), N-triisopropylsilyl 5-amino-7-azaindole (see Heureux, A. L. et al., Tetrahedron Lett. 2004, 45, 2317) (145 mg, 0.50 mmol), dppf (8.2 mg, 0.015 mmol), Pd2(dba)3 (9.1 mg, 0.010 mmol), sodium tert-butoxide (72 mg, 0.64 mmol) in toluene (8.0 mL) was heated in a seal tube at 110° C. for 16 h. The mixture was allowed to cool and saturated ammonium chloride (30 mL) was added and the mixture was extracted with ethyl acetate (3×25 mL). The combined organic layers were dried (anhydrous sodium sulfate), filtered and evaporated to yield a residue was purified by reverse phase preparative HPLC to provide 141b. (M+H)+=375.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate (3×25 mL)
  3. dry with materialThe combined organic layers were dried (anhydrous sodium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. customto yield a residue
  7. customwas purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-27f0a7af9cbb4ffca98cc2e60d002269
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

Loading…