3-Bromothiophene → HCID 58975533, compound

HRID 1178786Notes

Reaction equation

HRID 1178786 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Sn](CCCC)(CCCC)CCCC)[CH:15]=2)[N:10]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:9]1=[O:38])([CH3:4])([CH3:3])[CH3:2].Br[C:41]1[CH:45]=[CH:44][S:43][CH:42]=1>C1COCC1.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>[C:1]([O:5][C:6](=[O:39])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:41]3[CH:45]=[CH:44][S:43][CH:42]=3)[CH:15]=2)[N:10]([CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:9]1=[O:38])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 133833-BromothiopheneHCID 58975526HCID 58975526, compound

Product 1

HCID 58975533HCID 58975533, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4A (25 mg, 0.043 mmol) in degas sed THF (2 mL) was added tetrakis(triphenylphosphine)palladium (10 mg, 0.009 mmol), K2C3 (18 mg, 0.13 mmol), and 3-bromothiophene (21 mg, 0.13 mmol). The resulting mixture was heated at 70° for 16 h under argon. After cooling to RT, the mixture was filtered through Celite®, rinsing with CH2Cl2. The filtrate was evaporated under vacuum and the resulting residue was chromatographed on silica gel eluted with EtOAc in hex ane to obtain the title compound (14.5 mg, somewhat impure).

Workup

  1. temperatureThe resulting mixture was heated at 70° for 16 h under argon
  2. filtrationthe mixture was filtered through Celite®
  3. washrinsing with CH2Cl2
  4. customThe filtrate was evaporated under vacuum
  5. customthe resulting residue was chromatographed on silica gel
  6. washeluted with EtOAc in hex ane

Sources & evidence

ORD record
ord-aca787f13c4b428a9f15556ad3a689ff
Source dataset
uspto-grants-2007_10
Patent number
US07276608B2

Reaction notes

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