Morpholine → HCID 22730439, compound

HRID 2085787Notes

Reaction equation

HRID 2085787 reaction equation
Br[C:2]1[S:3][C:4]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:5]=2[C:6]=1[CH3:7].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:12][C:9]1[CH:10]=[CH:11][C:4]2[S:3][C:2]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]([CH3:7])[C:5]=2[CH:8]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 27355482-Bromo-5-chloro-3-methylbenzo[b]thiopheneHCID 23676156Sodium t-butoxide

Product 1

HCID 22730439HCID 22730439, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-5-chloro-3-methylbenzthiophene (523 mg, 2 mmol), morpholine (210 uL, 2.4 mmol), Pd2dba3 (37 mg, 0.04 mmol), BINAP (62 mg, 0.1 mmol), and sodium tert-butoxide (270 mg, 2.8 mmol) in toluene (5 mL) was stirred at 80° C. for 18 hours. The reaction mixture was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes to provide the desired product. MS (ESI(+)) m/e 268 (M+H)+.

Workup

  1. customThe reaction mixture was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-50a8aeac2e73475b84aad689adc92e0f
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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