Dimethylformamide → tert-Butyl 4-(2-(benzo[d]thiazol-2-ylethynyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

HRID 1772724Notes

Reaction equation

HRID 1772724 reaction equation
[C:1]([C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=3)[N:6]2[CH:30]=1)#[CH:2].Br[C:32]1[S:33][CH:34]=[CH:35][N:36]=1.CCN([CH:43]([CH3:45])[CH3:44])C(C)C.[CH3:46]N(C=O)C>[Cu]I.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.[CH-]1C=C(P(C2C=CC=CC=2)C2C=CC=CC=2)C=C1.Cl[Pd]Cl.[Fe+2]>[S:33]1[C:34]2[CH:46]=[CH:45][CH:43]=[CH:44][C:35]=2[N:36]=[C:32]1[C:2]#[C:1][C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[CH:28][CH:29]=3)[N:6]2[CH:30]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 764302-BromothiazoleHCID 81531DiisopropylethylamineHCID 117732303tert-Butyl 4-(2-ethynyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

Product 1

HCID 117732304tert-Butyl 4-(2-(benzo[d]thiazol-2-ylethynyl)-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Compound 81b (95.0 mg, 0.23 0 mmol) and 2-bromothiazole (430 mg, 2.00 mmol) were placed in a vial and purged with Argon. Anhydrous DMF (2 mL) and DIEA (0.410 mL, 2.35 mmol) were added. The mixture was degassed and purged with Argon. CuI (2.24 mg, 0.0120 mmol) and dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct (16.5 mg, 0.0230 mmol) were added. The reaction was stirred at rt for 4 h. The reaction was filtered through a pad of diatomaceous earth and the filter cake was rinsed with EtOAc. The combined filtrates were washed with brine and water, dried, and concentrated. The residue was purified with preparative TLC (EtOAc/dichloromethane; 3:7) to obtain compound 81c. Mass Spectrum (LCMS, ESI pos.): Calcd. for C30H28N5O3S: 538.2 (M+H). found: 538.5.

Workup

  1. custompurged with Argon
  2. customThe mixture was degassed
  3. custompurged with Argon
  4. filtrationThe reaction was filtered through a pad of diatomaceous earth
  5. washthe filter cake was rinsed with EtOAc
  6. washThe combined filtrates were washed with brine and water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified with preparative TLC (EtOAc/dichloromethane; 3:7)

Sources & evidence

ORD record
ord-5028abe7dca7455ebae43cc20c12019c
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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