Triethylamine → HCID 86606905, compound

HRID 1364573Notes

Reaction equation

HRID 1364573 reaction equation
[NH2:1][C:2]1[C:7](I)=[C:6]([O:9][CH2:10][CH3:11])[N:5]=[C:4]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[O:13])[CH:3]=1.[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])#[CH:27].C(N([CH2:37][CH3:38])CC)C>CN(C)C=O.[Cu]I>[CH3:25][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:12]([C:4]2[CH:3]=[C:2]([NH2:1])[C:7]([C:37]([Si:28]([CH3:30])([CH3:29])[CH3:26])=[CH:38][C:27]#[C:26][Si:28]([CH3:31])([CH3:30])[CH3:29])=[C:6]([O:9][CH2:10][CH3:11])[N:5]=2)=[O:13])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 66920681HCID 66920681, compound

Product 1

HCID 86606905HCID 86606905, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of Example 240B (95 mg, 0.2 mmol), ethynyltrimethylsilane (59 mg, 0.6 mmol), PdCl2 (Ph3P)2 (7 mg, 0.01 mmol), CuI (4 mg, 0.02 mmol) and triethylamine (40 mg, 0.4 mmol) in N,N-dimethylformamide (2 ml) was sealed in a tube and heated at 110° C. for 6 hours, checked with LC/MS until starting material disappeared. The mixture was filtered and the filtrate was partitioned between ethyl acetate and water (30 ml, 1:1). The organic layer was washed with brine, dried over MgSO4, filtered, and evaporated in vacuo. The crude product was purified on silica gel cartridge by Anal.ogix eluting with 100% ethyl acetate to give the titled compound (32 mg, 30%). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.03 (t, J=6.44 Hz, 1H), 7.87 (d, J=8.48 Hz, 2H), 7.55 (d, J=8.14 Hz, 2H), 7.06 (s, 1H), 6.75 (s, 1H), 6.05 (s, 2H) 4.57 (d, J=6.44 Hz, 2H), 4.36 (q, J=6.95 Hz, 2H), 3.17 (s, 3H), 1.29 (t, J=6.95 Hz, 3H), 0.21 (s, 9H), 0.11 (s, 9H); MS (APCI) m/z 544 [M+H]+, 542 [M−H]−.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was partitioned between ethyl acetate and water (30 ml, 1:1)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was purified on silica gel cartridge by Anal.ogix
  8. washeluting with 100% ethyl acetate

Sources & evidence

ORD record
ord-c00eb04ff6ef4c68bf3f05acac94f8ce
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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