Trityl chloride → HCID 22479811, compound

HRID 1353942Notes

Reaction equation

HRID 1353942 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[N:11]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:10]=[C:9]3[Br:21])=[N:2]1.[C:22]1([C:28](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>N1C=CC=CC=1.C(OCC)(=O)C>[Br:21][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([C:3]3[N:4]=[CH:5][N:1]([C:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:2]=3)[CH:7]=2)[N:11]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:10]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178419479HCID 178419479, compound

Product 1

HCID 22479811HCID 22479811, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

2-(5-(1H-1,2,4-Triazol-3-yl)-3-bromo-1H-indazolyl)perhydro-2H-pyran (15.05 g, 43.22 mmol), triphenylmethyl chloride (19.54 g, 70.09 mmol), and triethylamine (9.9 mL, 71.02 mmol) was taken up in pyridine (115 mL) and heated at 50° C. overnight. The reaction was quenched with methanol (10 mL), cooled to room temperature, and condensed. The brown oil was dissolved in ethyl acetate and washed with sodium bicarbonate (saturated aqueous). Upon sonication in a ultrasonic bath a white to yellow precipitate formed that was filtered and washed with 10% ethyl acetate in hexanes. The precipitate was dried in a vacuum oven overnight (23.80 g, 93% yield): ES-MS (m/z) 590 [M+1]+.

Workup

  1. customThe reaction was quenched with methanol (10 mL)
  2. temperaturecooled to room temperature
  3. customcondensed
  4. washwashed with sodium bicarbonate (saturated aqueous)
  5. customUpon sonication in a ultrasonic bath a white to yellow precipitate
  6. customformed
  7. filtrationthat was filtered
  8. washwashed with 10% ethyl acetate in hexanes
  9. customThe precipitate was dried in a vacuum oven overnight (23.80 g, 93% yield)

Sources & evidence

ORD record
ord-bc903ecf19894cd5814d7f91397ff8d7
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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