Dichloromethane → HCID 86664053, compound

HRID 712345Notes

Reaction equation

HRID 712345 reaction equation
Br[C:2]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][C:10]([CH2:18][CH3:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]2)[S:5][CH:6]=1.[CH2:20]([NH:22][C:23]([NH:25][C:26]1[S:27][C:28]2[C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)=[CH:33][C:32](B(O)O)=[CH:31][C:29]=2[N:30]=1)=[O:24])[CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl>CN(C=O)C.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.Cl[Pd]Cl.[Fe+2]>[CH2:18]([C:10]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:12][N:7]([C:4]2[S:5][CH:6]=[C:2]([C:32]3[CH:33]=[C:34]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[C:28]4[S:27][C:26]([NH:25][C:23](=[O:24])[NH:22][CH2:20][CH3:21])=[N:30][C:29]=4[CH:31]=3)[N:3]=2)[CH2:8][CH2:9]1)[CH3:19]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 66977057Ethyl 1-(4-bromothiazol-2-yl)-4-ethyl-piperidine-4-carboxylateHCID 727244832-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-ylboronic acid

Product 1

HCID 86664053HCID 86664053, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Ethyl 1-(4-bromothiazol-2-yl)-4-ethyl-piperidine-4-carboxylate (56 mg, 0.16 mmol), 2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl-boronic acid (50 mg, 0.15 mmol), and cesium carbonate (42 mg, 0.22 mmol) were suspended in DMF (1 mL) in a 5 mL microwave vessel. The resulting mixture was degassed with Ar for 5 min. [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (10 mg, 0.01 mmol), was added to the mixture, then the vessel sealed and heated at 120° C. for 60 min in a microwave. The mixture was cooled to rt then evaporated to dryness and the crude residue purified over a 12 g silica-gel column using a MeOH: DCM elution gradient (0-5%) to obtain the product as a viscous oil (30 mg, 36% yield). MS: 565.13 [M+H]+.

Workup

  1. additionwas added to the mixture
  2. customthe vessel sealed
  3. temperatureThe mixture was cooled to rt
  4. customthen evaporated to dryness
  5. customthe crude residue purified over a 12 g silica-gel column
  6. washDCM elution gradient (0-5%)

Sources & evidence

ORD record
ord-155c946d6c2b4b579265ee66295d9062
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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