HCID 9974875, compound → HCID 68183245, compound

HRID 1615533Notes

Reaction equation

HRID 1615533 reaction equation
C([Sn](CCCC)(CCCC)/[CH:6]=[CH:7]\[CH2:8][NH2:9])CCC.Br[C:19]1[N:20]=[C:21]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[S:22][C:23]=1[C:24]([O-:26])=O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:27]1([C:21]2[S:22][C:23]3[C:24](=[O:26])[NH:9][CH2:8][CH:7]=[CH:6][C:19]=3[N:20]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 9974875HCID 9974875, compoundHCID 86669798HCID 86669798, compound

Product 1

HCID 68183245HCID 68183245, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of Z-3-(tributylstannyl)-2-propen-1-amine (30.0 g, 86.7 mmol) and 4-bromo-2-morpholin-4-yl-1,3-thiazole-5-carboxylate (27.8 g, 86.7 mmol) in toluene (136 mL) was purged with argon, and then tetrakis(triphenylphosphinepalladium(0) (5.01 g, 4.33 mmol) was added. The reaction mixture was stirred at 120° C. under an atmosphere of argon for 5 days. The solvent was evaporated, then the residue was adsorbed onto silica gel then purified using column chromatography on silica gel (600 gr Analogix column, gradient DCM to 5% MeOH in DCM over 40 minutes) to give the product (3.44 g, 16%). LCMS: (AA) ES+ 252. 1H NMR (400 MHz, d6-DMSO) δ: 7.73 (s, 1H), 6.63 (d, J=10.3 Hz, 1H), 6.24 (dt, J=10.3, 6.6 Hz, 1H), 3.74-3.63 (m, 4H), 3.54-3.47 (m, 2H), 3.47-3.40 (m, 4H).

Workup

  1. customThe solvent was evaporated
  2. customthen purified
  3. customon silica gel (600 gr Analogix column, gradient DCM to 5% MeOH in DCM over 40 minutes)

Sources & evidence

ORD record
ord-f9d06f17ba874653b26ea3a784eb97bb
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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