1-Bromo-2-methylpropane → HCID 22951382, compound

HRID 276303Notes

Reaction equation

HRID 276303 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[C:3]=1[CH3:10].I[C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[S:20])=[C:14]([CH3:21])[C:13]=1[CH3:22].[CH2:23](Br)[CH:24]([CH3:26])[CH3:25].[CH3:28][Si:29]([C:32]#[CH:33])([CH3:31])[CH3:30]>CCN(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:9][C:4]1[C:3]([CH3:10])=[C:2]([I:1])[CH:8]=[CH:7][C:5]=1[N:6]=[C:19]1[S:20][CH2:14][C:15]2([CH2:13][CH2:12][CH2:17][CH2:16]2)[NH:18]1.[CH3:21][C:14]1[C:13]([CH3:22])=[C:12]([C:33]#[C:32][Si:29]([CH3:31])([CH3:30])[CH3:28])[CH:17]=[CH:16][C:15]=1[N:18]=[C:19]1[S:20][CH2:4][C:5]2([CH2:3][CH2:2][CH2:8][CH2:7]2)[N:6]1[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

9

Reactant 4

HCID 65551-Bromo-2-methylpropaneHCID 66111TrimethylsilylacetyleneHCID 140402864-Iodo-2,3-dimethylbenzenamineHCID 18316004HCID 18316004, compound

Product 2

HCID 22951382HCID 22951382, compoundYield 59%HCID 178429777HCID 178429777, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

4-Iodo-2,3-dimethylaniline was converted into 4-iodo-2,3-dimethylphenyl isothiocyanate in a manner analogous to Method A2b. 2-(2,3-Dimethyl-4-iodophenylimino)-3-thia-1-azaspiro[4.4]nonane was prepared in a manner analogous to that described in Method C2a, then was alkylated with isobutyl bromide in a manner analogous to that described in Method D2a. A mixture of the iodophenyl compound (0.009 g, 0.021 mmol), (trimethylsilyl)acetylene (30 mL, 0.21 mmol), Pd(PPh3)2Cl2 (0.005 g) and CuI (0.012 g, 0.063 mmol) in Et3N (2 mL) was stirred at room temp. for 18 h. The resulting slurry was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative TLC (2% EtOAc/hex) to give 2-(2,3-dimethyl-4-(2-trimethylsilyl-1-ethynyl)phenylimino)-1-isobutyl-3-thia-1-azaspiro[4.4]nonane (0.005 g, 59%).

Workup

  1. filtrationThe resulting slurry was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative TLC (2% EtOAc/hex)

Sources & evidence

ORD record
ord-fcd77aa306fe4077b55c282fb1dc3cb7
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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