Triethylamine → HCID 68431066, compound

HRID 889259Notes

Reaction equation

HRID 889259 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([N:15]2[S:19](=[O:21])(=[O:20])[NH:18][C:17](=[O:22])[CH2:16]2)=[C:13]([F:23])[C:12](Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][C:26]([CH3:34])([CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[C:27]#[N:28].C(N(CC)CC)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:33]=[CH:32]\[CH2:31][CH2:30][CH2:29][C:26]([CH3:34])([CH3:25])[C:27]#[N:28])=[C:13]([F:23])[C:14]=1[N:15]1[CH2:16][C:17](=[O:22])[NH:18][S:19]1(=[O:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 68429374HCID 68429374, compoundHCID 85622393HCID 85622393, compound

Product 1

HCID 68431066HCID 68431066, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(6-benzyloxy-3-bromo-2-fluorophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (1.0 g, 2.4 mmol), 2,2-dimethylhept-6-enenitrile (493 mg, 3.6 mmol), Pd(OAc)2 (108 mg, 0.48 mmol), triethylamine (1.67 mL, 12 mmol) and 2-(di-t-butylphosphino)biphenyl (286 mg, 0.96 mmol) in acetonitrile (15 mL) is stirred in a microwave apparatus at 100° C. for 10 min. It is then filtered and the solvent is removed to give the title compound as a red liquid. The material is used in the next step without purification.

Workup

  1. filtrationIt is then filtered
  2. customthe solvent is removed

Sources & evidence

ORD record
ord-0cfdbd8aef894a99bd8f82750dc185b3
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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