1-Bromonaphthalene → tert-Butyl 4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

HRID 549944Notes

Reaction equation

HRID 549944 reaction equation
C(N(CC)CC)C.C[Si]([C:12]#[C:13][C:14]1[N:15]=[C:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[S:17][CH:18]=1)(C)C.Br[C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O.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.[Cu]I>[C:41]1([C:12]#[C:13][C:14]2[N:15]=[C:16]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[S:17][CH:18]=2)[C:42]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:38]=[CH:39][CH:40]=1

Participants

9

Reactant 4

HCID 70011-BromonaphthaleneHCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 67157073Tert-butyl 4-{4-[(trimethylsilyl)ethynyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Product 1

HCID 67157278tert-Butyl 4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (95 mg), copper(I) iodide (31 mg) and triethylamine (200 mg) are added to a solution of tert-butyl 4-{4-[(trimethylsilyl)ethynyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (XI-1, 600 mg) and 1-bromonaphthalene (375 mg) in degassed N,N-dimethylformamide. After heating to 85° C., tetra-n-butylammonium fluoride (1M in THF, 1.81 ml) is added dropwise. The reaction mixture is then diluted with water and extracted with ethyl acetate. The organic extracts are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives tert-butyl 4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (576 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts are dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customAfter chromatographic purification

Sources & evidence

ORD record
ord-7b555b457fe94adfac93aae15ac2cc7a
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

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