Diethylamine → HCID 12090793, compound

HRID 1176156Notes

Reaction equation

HRID 1176156 reaction equation
Br[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5](Br)=[CH:4][CH:3]=1.C(N[CH2:15][CH3:16])C.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>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.C1COCC1>[CH3:17][Si:18]([C:21]#[C:22][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([C:16]#[C:15][Si:18]([CH3:20])([CH3:19])[CH3:17])=[CH:4][CH:3]=1)([CH3:20])[CH3:19]

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 66111TrimethylsilylacetyleneHCID 6263614,7-Dibromo-2,1,3-benzothiadiazole

Product 1

HCID 12090793HCID 12090793, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

4,7-Dibromobenzo[c][1,2,5]thiadiazole (1.02 g, 3.47×10−3 mol), Pd(PPh3)4 (0.207 g, 1.79×10−4 mol), CuI (0.029 g, 1.5×10−4 mol), THF (30 ml), diethylamine (3.0 ml) and (trimethylsilyl)acetylene (6.00 ml, 4.25×10−2 mol) were added to a 100-ml Schlenk tube. N2 was bubbled through the mixture for 5 min, following which the reaction was stirred at 45° C. for 20 h under N2. After cooling, the solvent was evaporated and the residue was chromatographed on silica gel with 1:1 hexanes:CHCl3 as the eluant. Yield=1.05 g (92% based on 1.02 g of 4,7-dibromobenzothiadiazole). 1H NMR (360 MHz, CDCl3): δ 7.70 (s, 2H, Ph-H), 0.33 (s, 18H, —Si—CH3). Chemical Ionization MS m/z: 328.0880 (M+) (calcd 328.089).

Workup

  1. customN2 was bubbled through the mixture for 5 min
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. customthe residue was chromatographed on silica gel with 1:1 hexanes

Sources & evidence

ORD record
ord-06664e0ba9d24fa7aa044dd41bf0ef90
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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