Triethylamine → HCID 12093792, compound

HRID 1838456Notes

Reaction equation

HRID 1838456 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23](=[O:24])[C:22]3[NH:21][C:20](C4C=CC(I)=CC=4)=[N:19][C:18]=3[N:17]([CH2:32][CH2:33][CH3:34])[C:16]2=[O:35])=[CH:11][CH:10]=1.B(O)O.CC[N:41]([CH2:44][CH3:45])CC>CC([O-])=O.CC([O-])=O.[Cu+2].C(Cl)Cl>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23](=[O:24])[C:22]3[N:21]([C:4]4[CH:5]=[C:45]([CH:7]=[CH:8][CH:3]=4)[C:44]#[N:41])[CH:20]=[N:19][C:18]=3[N:17]([CH2:32][CH2:33][CH3:34])[C:16]2=[O:35])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61668Boronic AcidHCID 69891334HCID 69891334, compound

Product 1

HCID 12093792HCID 12093792, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A 25-mL round bottom flask equipped with a stir bar was charged with 6 (180 mg, 0.46 mmol) and CH2Cl2 (5.0 mL). The reaction mixture was treated with boronic acid 7 (135 mg, 0.92 mmol), Et3N (0.13 mL, 0.92 mmol), crushed 4 A mol. sieves (720 mg, 4× weight) and Cu(OAc)2 (167 mg, 0.92 mmol) at 25° C. After 12 h, the reaction was filtered through a plug of Celite® and washed with CH2Cl2 (100 mL). The organic phase was washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography of the residue on silica (40-50% EtOAc/hexanes) provided 8 (100 mg, 44%) as a white solid: ESI-MS m/z: [C28H23N5O2S+H]+ 494; 1H NMR (300 MHz, CDCl3) δ 7.90-7.00 (m, 13H), 4.19 (t, J 7.5 Hz, 2H), 2.33 (s, 3H), 1.99-1.85 (m, 2H), 1.03 (t, J=7.3 Hz, 3H).

Workup

  1. customA 25-mL round bottom flask equipped with a stir bar
  2. customcrushed 4 A mol
  3. customat 25° C
  4. filtrationthe reaction was filtered through a plug of Celite®
  5. washwashed with CH2Cl2 (100 mL)
  6. washThe organic phase was washed with brine (50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54ca9684943f46a2b99bd8e3d0726b89
Source dataset
uspto-grants-2004_01
Patent number
US06673810B2

Reaction notes

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