Acetonitrile → HCID 71661721, compound

HRID 64244Notes

Reaction equation

HRID 64244 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[S:16][CH:15]=[N:14][CH:13]=3)=[N:9][C:8]=2[CH:17]=1)=[N+:2]=[N-:3].[C:18](OCC)(=[O:20])[CH3:19].[CH3:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].CCN(C(C)C)C(C)C.[C:39](#N)[CH3:40]>[Cu]I>[O:20]([CH:18]([C:39]1[N:3]=[N:2][N:1]([C:4]2[CH:5]=[CH:6][C:7]3[O:11][C:10]([C:12]4[S:16][CH:15]=[N:14][CH:13]=4)=[N:9][C:8]=3[CH:17]=2)[CH:40]=1)[CH3:19])[C:26]1[CH:25]=[CH:24][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 21226206Ethyl acetate hexane2×HCID 716615455-Azido-2-(thiazol-5-yl)benzo[d]oxazole

Product 1

HCID 71661721HCID 71661721, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

A mixture of 5-azido-2-(thiazol-5-yl) benzo[d]oxazole 29 (37 mg, 0.15 mmol) and (But-3-yn-2-yloxy) Benzene 28 (20 mg, 0.13 mmol) were dissolved in anhydrous acetonitrile (3 mL) under nitrogen atmosphere. Then added DIPEA (53 mg, 0.40 mmol) stirred at rt for 10 min. After that added CuI (51.7 mg, 0.27 mmol) portion wise, stirred for 30 mins. The mixture was quenched with NH4Cl, diluted with water and extracted with DCM. Organic layer dried on MgSO4, filtered and concentrated under vacuo. Corresponding crude product was isolated by using silica column (ethyl acetate/n-hexane 50:50) to furnish 5-(4-(1-phenoxyethyl)-1H-1, 2,3-triazol-1-yl)-2-(thiazol-5-yl) benzo [d]oxazole 30 (43 mg, 84%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 1.77 (d, J=6.4 Hz, 3H), 5.69 (q, J=6.4 Hz, 1H), 6.90-6.97 (m, 3H), 7.22-7.24 (m, 2H), 7.66 (d, J=8.8 Hz, 1H), 7.74 (dd, J1=8 Hz, J2=2 Hz, 1H), 7.90 (s, 1H), 7.99 (d, J=2 Hz, 1H), 8.66 (s, 1H), 8.98 (s, 1H); 13C NMR (Pyridine-d5, 100 MHz) δ 22.1, 69.5, 112.3, 112.5, 116.6, 119.1, 121.7, 121.8, 125.8, 130.3, 135.3, 143.2, 146.9, 150.5, 151.1, 158.5, 159.0, 159.3; ESI-HRMS for C20H16N5O2S (M+H)+ calcd. 390.1025. found 390.1031.

Workup

  1. customThe mixture was quenched with NH4Cl
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. customOrganic layer dried on MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuo
  7. customwas isolated

Sources & evidence

ORD record
ord-70f9222df85d42d4acf62bdbb5a6c4be
Source dataset
uspto-grants-2016_09
Patent number
US09447134B2

Reaction notes

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