Triethylamine → methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-phenylprop-1-ynyl)thiazole-4-carboxylate

HRID 333880Notes

Reaction equation

HRID 333880 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25](I)=[C:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[CH2:41]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:42]#[CH:43].C(N(CC)CC)C>O1CCCC1.C(OCC)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([C:43]#[C:42][CH2:41][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[C:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 575753BenzylacetyleneHCID 59447651methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-iodothiazole-4-carboxylate

Product 1

HCID 90000452methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-phenylprop-1-ynyl)thiazole-4-carboxylate

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 15B (1.69 g) in tetrahydrofuran (30 mL) was added bis(triphenylphosphine)palladium (II) dichloride (88 mg), CuI (4.8 mg), prop-2-ynylbenzene (584 mg) and triethylamine (1.5 mL). The mixture was stirred at room temperature for 3 hours, diluted with diethyl ether and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography, eluting with 10% ethyl acetate in hexanes, to give the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b82cbdc066a34ae9954b1152f2cf03d0
Source dataset
uspto-grants-2014_11
Patent number
US08883784B2

Reaction notes

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