Ethyl Acetate → HCID 21883935, compound

HRID 722262Notes

Reaction equation

HRID 722262 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[NH:18][C:19]([C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[O:20].[CH3:31][CH2:32][N:33](C(C)C)C(C)C.BrCC#N.CCOC(C)=O>C(#N)C>[Cl:30][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:19]([NH:18][CH:10]1[CH2:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]1[NH:8][CH2:31][C:32]#[N:33])=[O:20])=[CH:29]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 69585646HCID 69585646, compound

Product 1

HCID 21883935HCID 21883935, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-[1-Amino-2,3-dihydro-1H-inden-2-yl]-5-chloro-1H-indole-2-carboxamide trifluoroacetic acid salt (Method 4, 220 mg, 0.5 mmol), DIPEA (260 μL, 1.5 mmol) and bromoacetonitrile (37 μL, 0.55 mmol) in acetonitrile (5 mL) were heated in a microwave to 180° C. for 1 min. EtOAc (30 mL) was added and the mixture washed with water,(2×10 mL), brine (10 mL), dried (MgSO4) and evaporated. The residue was purified by column chromatography (EtOAc:Hexane 1:1) to afford the title compound (110 mg, 60%) as a white foam.

Workup

  1. washthe mixture washed with water,(2×10 mL), brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography (EtOAc:Hexane 1:1)

Sources & evidence

ORD record
ord-1d0c664558564d44a433de62beddf82d
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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