Benzo(b)thiophene, 3-bromo- → HCID 12004311, compound

HRID 2241977Notes

Reaction equation

HRID 2241977 reaction equation
Br[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[CH2:24][CH2:23][N:22]([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH2:21][CH2:20]1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>O1CCCC1.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]>[S:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]([N:28]2[CH2:27][CH2:26][CH:25]([N:22]3[CH2:23][CH2:24][N:19]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[O:12][CH3:11])[CH2:20][CH2:21]3)[CH2:30][CH2:29]2)=[CH:3]1

Participants

7

Reactant 4

HCID 123250Benzo(b)thiophene, 3-bromo-HCID 1530394HCID 1530394, compoundHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 12004311HCID 12004311, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromo-benzothiophene (commercially available, 0.232 g) and 4-(4-(2-methoxyphenyl)piperazin-1-yl)piperidine (Step 2, 0.30 g) in tetrahydrofuran was added sodium tert-butoxide (0.15 g), tris-(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.10 g) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)-biphenyl (CYMAP, 0.01 g). The reaction was heated at reflux for 24 hours. It was then cooled and filtered through celite. The filtrate was evaporated and purified by flash chromatography on silica gel using ethyl acetate/hexanes to give 0.10 g of the desired product. MP: 156-158° C.; MS (ES) m/z (relative intensity): 408 (M+H)+ (100).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 24 hours
  3. temperatureIt was then cooled
  4. filtrationfiltered through celite
  5. customThe filtrate was evaporated
  6. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c91574b4ac8644ad99525e253cdd1ec9
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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